【结 构 式】 |
【分子编号】40671 【品名】1-[(hydroxyamino)methyl]benzene; N-benzylhydroxylamine 【CA登记号】 |
【 分 子 式 】C7H9NO 【 分 子 量 】123.1546 【元素组成】C 68.27% H 7.37% N 11.37% O 12.99% |
合成路线1
该中间体在本合成路线中的序号:The protection of the amino group of 3(S)-amino-1-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (I) with tert-butoxycarbonyl anhydride gives the carbamate (II), which is methylated with NaH and methyl iodide in DMF yielding the N-methoxy derivative (III). The deprotection of (III) with TFA and its condensation with 2(R)-isobutylsuccinic acid 4-tert-butyl monoester (IV) by means of DCC and HOBT in DMF affords the succinamic ester (V), which is hydrolyzed with TFA to give the succinamic acid (VI). The reaction of (VI) with O-benzylhydroxylamine by means of HOBT in DMF yields the benzyl hydroxamate (VII), which is finally debenzylated by hydrogenation with H2 over Pd/C in ethanol.
【1】 Sakamoto, M.; Imaoka, T.; Motoyama, M.; Yamamoto, Y.; Takasu, H. (Otsuka Pharmaceutical Co., Ltd.); Carbostyril derivs. as matrix metalloproteinases inhibitors. EP 0641323; JP 1995157470; WO 9421612 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
40671 | 1-[(hydroxyamino)methyl]benzene; N-benzylhydroxylamine | C7H9NO | 详情 | 详情 | ||
(I) | 30951 | (3S)-3-amino-1-hydroxy-3,4-dihydro-2(1H)-quinolinone | C9H10N2O2 | 详情 | 详情 | |
(II) | 30952 | tert-butyl (3S)-1-hydroxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinylcarbamate | C14H18N2O4 | 详情 | 详情 | |
(III) | 30953 | tert-butyl (3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinylcarbamate | C15H20N2O4 | 详情 | 详情 | |
(IV) | 25393 | (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-4-methylpentanoic acid | C12H22O4 | 详情 | 详情 | |
(V) | 30954 | tert-butyl (3R)-3-([[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]amino]carbonyl)-5-methylhexanoate | C22H32N2O5 | 详情 | 详情 | |
(VI) | 30955 | (3R)-3-([[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]amino]carbonyl)-5-methylhexanoic acid | C18H24N2O5 | 详情 | 详情 | |
(VII) | 30956 | (2R)-N(4)-(benzyloxy)-2-isobutyl-N(1)-[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]butanediamide | C25H31N3O5 | 详情 | 详情 |