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【结 构 式】

【分子编号】45884

【品名】ethyl 2-[[(benzyloxy)imino]methyl]hexanoate

【CA登记号】

【 分 子 式 】C16H23NO3

【 分 子 量 】277.36356

【元素组成】C 69.29% H 8.36% N 5.05% O 17.31%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

Claisen reaction between ethyl caproate (I) and ethyl formate (II) in the presence of NaOEt affords formyl derivative (III), which is then condensed with O-benzyl hydroxylamine hydrochloride (IV) by means of NaOAc in EtOH/H2O to yield derivative (V). Hydrolysis of the ethyl ester moiety of (V) by treatment with aqueous NaOH in MeOH provides carboxylic acid (VI), which is coupled to tert-leucine N,N-dimethylamide (VII) by means of EDC and HOAt to furnish compound (VIII). Reduction of the oxime moiety of (VIII) with NaCNBH3 in HOAc affords a mixture of diastereoisomers from which (R)-(IX) is separated by flash chromatography. Finally, treatment of (R)-(IX) with N-formyl-benzotriazole (HCOBt) in THF provides formamide (X), whose benzyl group is then removed by hydrogenation over Pd/C in MeOH.

1 Spavold, Z.M.; Launchbury, S.; Clements, J.M.; Hunter, M.G.; Davies, S.J.; Pratt, L.M.; Beckett, R.P.; Whittaker, M. (British Biotech Pharmaceuticals Ltd.); Antibacterial agents. WO 9939704 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIIIa) 45887 (2R)-2-[[(benzyloxy)imino]methyl]-N-[(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl]hexanamide C22H35N3O3 详情 详情
(VIIIb) 45890 (2S)-2-[[(benzyloxy)imino]methyl]-N-[(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl]hexanamide C22H35N3O3 详情 详情
(I) 51702 Ethyl caproate; Ethyl n-Caproate; Caproic acid ethyl ester; n-Caproic acid ethylester; Capronic Ether; Isoamyl acetate; Hexanoic acid ethyl ester; Ethyl hexanoate 123-66-0 C8H16O2 详情 详情
(II) 16602 ethyl formate 109-94-4 C3H6O2 详情 详情
(III) 45886 (2S)-2-amino-N,N,3,3-tetramethylbutanamide C8H18N2O 详情 详情
(IV) 14640 O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene 622-33-3 C7H9NO 详情 详情
(V) 45884 ethyl 2-[[(benzyloxy)imino]methyl]hexanoate C16H23NO3 详情 详情
(VI) 45885 2-[[(benzyloxy)imino]methyl]hexanoic acid C14H19NO3 详情 详情
(VII) 45886 (2S)-2-amino-N,N,3,3-tetramethylbutanamide C8H18N2O 详情 详情
(IX) 45888 (2R)-2-[[(benzyloxy)amino]methyl]-N-[(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl]hexanamide C22H37N3O3 详情 详情
(X) 45889 (2R)-2-[[(benzyloxy)(formyl)amino]methyl]-N-[(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl]hexanamide C23H37N3O4 详情 详情
Extended Information