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    CHIRALLY SUBSTITUTED 2-IMIDAZOLIN-5-ONES
    2.
    发明专利
    CHIRALLY SUBSTITUTED 2-IMIDAZOLIN-5-ONES 未知

    公开(公告)号：CA1100974A

    公开(公告)日：1981-05-12

    申请号：CA293445

    申请日：1977-12-20

    Applicant: BASF AG

    Inventor： SCHOELLKOPF ULRICH ,  HAUSBERG HANS-HEINRICH ,  BOELL WALTER ,  MAY HANS-JOACHIM ,  KOENIG HORST

    IPC: C07C67/00 ,  C07C227/00 ,  C07C227/22 ,  C07C227/34 ,  C07D233/70 ,  C07D317/00 ,  C07D333/00 ,  C07D405/06 ,  C07D409/06

    Abstract: : The present invention relates to chirally substituted 2-imidazolin-5-ones of the general formula I : (I) where R1 is L-.alpha.-phenylethyl, (+)-3-pinyl-methyl, (-)-no-pinyl, or L-.alpha.-carbo-tert.-butoxy-ethyl, R2 is hydrogen, methyl, benzyl or phenyl, R3 and R4 are different from one another and R3 is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by methoxy, methylthio, dimethylamino, cyano and carbethoxy, benzyl or benzyl which is monoor disubstituted by alkoxy containing 1 to 4 carbon atoms, acyloxy and monosubstituted by chloro, bromo, nitro or methylenedioxy, or phenyl, and R4 is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by methoxy, methylthio, dimethylamino, cyano and carbethoxy, benzyl or benzyl which is mono- or disubstituted by alkoxy containing 1 to 4 carbon atoms, acyloxy and monosubstituted by chloro, bromo, nitro or methylenedioxy, or allyl, or R4 is additionally a radical selected from the group consisting of naphtyl-methyl, thienyl-methyl, benzothienyl-methyl and bromo-benzofuranyl-methyl. These compounds are used an intermediates for the preparation of optically active aminoacids, especially of optically active .alpha.-substituted aminoacids.

    3.
    发明专利
    未知

    公开(公告)号：DE58907247D1

    公开(公告)日：1994-04-21

    申请号：DE58907247

    申请日：1989-09-09

    Applicant: BASF AG

    Inventor： SCHOELLKOPF ULRICH ,  GROTH ULRICH ,  LANGE MEINOLF

    IPC: C07K1/02 ,  C07K1/12

    Abstract: PCT No. PCT/EP89/01050 Sec. 371 Date Jul. 17, 1990 Sec. 102(e) Date Jul. 17, 1990 PCT Filed Sep. 9, 1989 PCT Pub. No. WO90/03386 PCT Pub. Date Apr. 5, 1990.Process for producing dipeptides from non-proteinogenic amino acids with terminal carbon atoms.

    Diastereomeric 4,4-di:substd.-2-imidazolin-5-one derivs. - prepd. by asymmetric induction, intermediates for optically pure aminoacid(s) such as methyl-DOPA
    6.
    发明专利
    Diastereomeric 4,4-di:substd.-2-imidazolin-5-one derivs. - prepd. by asymmetric induction, intermediates for optically pure aminoacid(s) such as methyl-DOPA 未知

    公开(公告)号：DE2658942A1

    公开(公告)日：1978-07-06

    申请号：DE2658942

    申请日：1976-12-24

    Applicant: BASF AG

    Inventor： SCHOELLKOPF ULRICH ,  HAUSBERG HANS-HEINRICH DIPL CH ,  MAY HANS-JOACHIM DIPL CHEM DR ,  KOENIG HORST DIPL CHEM DR

    IPC: C07D233/70

    Abstract: Imidazoline-5-one derivs. of formula (I) are new: R1 is the optical active residue of a primary amine or aminoacid. R2 is H, 1-4C alkyl, benzyl or phenyl. R3 is 1-4C alkyl (opt. substd. by alkoxy, alkylthio or dialkyamino (all 1-4C alkyl), benzyloxy, benzylthio, 1-4C acyloxy, CN, 2-5C carbalkoxy, benzoyl or phenyl (the rings opt. substd. by 103 halo, NO2, 1-4C alkyl, alkoxy, or alkylthio, benzyloxy, 1-4C acyloxy or acylamino, or by one phenoxy (itself opt. substd by 1-4C alkoxy or acyloxy), CF3 or methylenedioxy), or R3 is allyl or phenyl. R4 is 1-6C alkyl opt. substd. by alkoxy, alkylthio or dialkylamino (all 1-4C alkyl), piperidino, pyrrolidino, benzyloxy, benzylthio, CN, 2-5C carbalkoxy, benzoyl or phenyl (both opt. substd. as for corresp. gps. R3), or R4 is ClCH2 or allyl. Q is pyridyl, furyl, thienyl, naphthyl, benzothienyl or bromobenzofuran. Where R3 and R4 are different, (I) are intermediates (by conventional hydrolysis) for optically active alpha-e ethyl-arylalanines, e.g. alpha-methyl-dopa (an antihypertensive) and alpha-methyltyrosine (a tranquilliser). (I) are prepd. by alkylation of corresp. cpds. (I) where R4 is H alkylation at the 4-posn. proceeds with nearly 100% asymmetric induction (the nature of R1 determines the configuration at this position) and practically no O-alkylation occurs. In an example, 1-L-alpha-phenylethyl-4-methyl-4-benzyl-2-imidazoline-5-one was prepd. from the L-alpha-phenylethylamide of alpha-isocyanopropionic acid/n-BuLi and benzyl bromide.

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