【结 构 式】 |
【分子编号】45885 【品名】2-[[(benzyloxy)imino]methyl]hexanoic acid 【CA登记号】 |
【 分 子 式 】C14H19NO3 【 分 子 量 】249.3098 【元素组成】C 67.45% H 7.68% N 5.62% O 19.25% |
合成路线1
该中间体在本合成路线中的序号:(VI)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 |