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【结 构 式】

【分子编号】48364

【品名】tert-butyl (1R)-2-amino-1-methyl-2-thioxoethylcarbamate

【CA登记号】

【 分 子 式 】C8H16N2O2S

【 分 子 量 】204.29332

【元素组成】C 47.03% H 7.89% N 13.71% O 15.66% S 15.7%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIII)

N-Boc-D-Alanine (XI) is converted to the corresponding amide (XII) by reaction with ammonia in the presence of EDC and HOBt. Subsequent treatment of (XII) with Belleau's reagent (2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide) furnishes thioamide (XIII). S-Alkylation of thioamide (XIII) with ethyl bromopyruvate (XIV) gives intermediate (XV), which is cyclized to thiazole (XVI) upon treatment with trifluoroacetic anhydride and 2,6-lutidine. After saponification of the ester group of (XVI) with LiOH, the resultant acid (XVII) is coupled with tripeptide (X) to provide precursor (XVIII).

1 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 58834 methyl 2-{[(2S)-2-{[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate C26H29N5O5 详情 详情
(XI) 15859 Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid 7764-95-6 C8H15NO4 详情 详情
(XII) 46750 tert-butyl (1R)-2-amino-1-methyl-2-oxoethylcarbamate C8H16N2O3 详情 详情
(XIII) 48364 tert-butyl (1R)-2-amino-1-methyl-2-thioxoethylcarbamate C8H16N2O2S 详情 详情
(XIV) 25183 ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate 70-23-5 C5H7BrO3 详情 详情
(XV) 58835 ethyl 3-({(2R)-2-[(tert-butoxycarbonyl)amino]propanimidoyl}sulfanyl)-2-oxopropanoate C13H22N2O5S 详情 详情
(XVI) 48366 ethyl 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-1,3-thiazole-4-carboxylate C13H20N2O4S 详情 详情
(XVII) 58836 2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazole-4-carboxylic acid C11H16N2O4S 详情 详情
(XVIII) 58837 methyl 2-{[(2S)-2-{[(2S)-2-{[(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate C37H43N7O8S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IX)

N-Boc-D-alanine (VII) was converted into amide (VIII) via activation as the corresponding mixed anhydride with isobutyl chloroformate. Treatment of amide (VIII) with Lawesson’s reagent gave thioamide (IX). Coupling of (IX) with ethyl bromopyruvate (X) produced the intermediate hydroxythiazoline (XI), which was further dehydrated using trifluoroacetic anhydride to afford the fully protected thiazole amino acid (XII). Removal of the Boc protecting group of (XII) to give (XIII) was achieved by treatment with either trifluoroacetic acid or acetyl chloride in EtOH.

1 Xia, Z.; Smith, C.D.; Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance. J Org Chem 2001, 66, 10, 3459.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 15859 Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid 7764-95-6 C8H15NO4 详情 详情
(VIII) 46750 tert-butyl (1R)-2-amino-1-methyl-2-oxoethylcarbamate C8H16N2O3 详情 详情
(IX) 48364 tert-butyl (1R)-2-amino-1-methyl-2-thioxoethylcarbamate C8H16N2O2S 详情 详情
(X) 25183 ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate 70-23-5 C5H7BrO3 详情 详情
(XI) 48365 ethyl 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-4-hydroxy-4,5-dihydro-1,3-thiazole-4-carboxylate C13H22N2O5S 详情 详情
(XII) 48366 ethyl 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-1,3-thiazole-4-carboxylate C13H20N2O4S 详情 详情
(XIII) 48367 ethyl 2-[(1R)-1-aminoethyl]-1,3-thiazole-4-carboxylate C8H12N2O2S 详情 详情
Extended Information