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【结 构 式】

【分子编号】27845

【品名】benzyl (3R)-2-oxooxetanylcarbamate

【CA登记号】

【 分 子 式 】C11H11NO4

【 分 子 量 】221.21268

【元素组成】C 59.73% H 5.01% N 6.33% O 28.93%

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:(IV)

The reaction of N-(tert-butoxycarbonyl)-L-phenylalanine-N-carboxyanhydride (I) with N-methylethylenediamine (II) gives the phenyalaninamide (III), which is condensed with the N-protected chiral azetidinone (IV) by means of Cs2CO3 to yield the diaminopropionic acid derivative (V). The condensation of (V) with glycine tert-butyl ester (VI) by means of BOP and DIEA affords the peptide (VII), which, after deprotection with H2 over Pd/C, is condensed with 4-O-benzyl-L-tyrosine (VIII) by means of BOP and DIEA giving the acyclic precursor (IX). The deprotection of (IX) with TFA, followed by cyclization by means of EDC, HOAt, DIEA and DCM in DMF provides the protected cyclic precursor (X), which is finally deprotected by hydrogenation with H2 over Pd black in ethanol.

1 DeHaven, R.; Dang, T.; Daubert, J.; Yaksh, T.L.; Zhang, L.; Goodman, M.; Shreder, K.; Umeno, H.; Synthesis and biological activity of a novel methylamine-bridged enkephalin analogue (MABE): A new route to cyclic peptides and peptidomimetics. J Med Chem 1998, 41, 14, 2631.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27837 tert-butyl (4S)-4-benzyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate 142955-51-9 C15H17NO5 详情 详情
(II) 27777 N-(2-aminoethyl)-N-methylamine 109-81-9 C3H10N2 详情 详情
(III) 27838 tert-butyl (1S)-1-benzyl-2-[[2-(methylamino)ethyl]amino]-2-oxoethylcarbamate C17H27N3O3 详情 详情
(IV) 27845 benzyl (3R)-2-oxooxetanylcarbamate C11H11NO4 详情 详情
(V) 27839 (6S,13R)-6-benzyl-13-[[(benzyloxy)carbonyl]amino]-2,2,11-trimethyl-4,7-dioxo-3-oxa-5,8,11-triazatetradecan-14-oic acid C28H38N4O7 详情 详情
(VI) 27841 tert-butyl 2-aminoacetate;tert-butyl glycinate;Glycine tert-butyl ester 6456-74-2 C6H13NO2 详情 详情
(VII) 27840 tert-butyl (6S,13R)-6-benzyl-13-[[(benzyloxy)carbonyl]amino]-2,2,11-trimethyl-4,7,14-trioxo-3-oxa-5,8,11,15-tetraazaheptadecan-17-oate C34H49N5O8 详情 详情
(VIII) 27842 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[4-(benzyloxy)phenyl]propionic acid C24H23NO5 详情 详情
(IX) 27843 tert-butyl (6S,13R)-6-benzyl-13-([(2S)-2-[[(benzyloxy)carbonyl]amino]-3-[4-(benzyloxy)phenyl]propanoyl]amino)-2,2,11-trimethyl-4,7,14-trioxo-3-oxa-5,8,11,15-tetraazaheptadecan-17-oate C50H64N6O10 详情 详情
(X) 27844 benzyl (1S)-2-[[(6S,12R)-6-benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraazacyclotridecan-12-yl]amino]-1-[4-(benzyloxy)benzyl]-2-oxoethylcarbamate C41H46N6O7 详情 详情
Extended Information