Water → tert-butyl (3S)-3-{[(2S)-2-(2-{[2-({[(tert-butoxy)carbonyl]amino}methyl)-1,3-thiazol-4-yl]formamido}-2-methylpropanamido)-3-methylbutanoyl]oxy}pent-4-enoate

HRID 405690노트

반응식

HRID 405690 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=O)=[O:16])[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[NH2:33][C@@H:34]([CH:49]([CH3:51])[CH3:50])[C:35]([O:37][C@H:38]([CH:47]=[CH2:48])[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:36].O>CN(C)C=O.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]([CH3:23])([CH3:22])[C:19]([NH:33][C@@H:34]([CH:49]([CH3:51])[CH3:50])[C:35]([O:37][C@H:38]([CH:47]=[CH2:48])[CH2:39][C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])=[O:36])=[O:21])=[O:16])[N:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 25053306(S)-tert-butyl 3-((S)-2-amino-3-methylbutanoyloxy)pent-4-enoateHCID 679919852-(2-((Tert-butoxycarbonylamino)methyl)thiazole-4-carboxamido)-2-methylpropanoic acid

생성물 1

HCID 86691464tert-butyl (3S)-3-{[(2S)-2-(2-{[2-({[(tert-butoxy)carbonyl]amino}methyl)-1,3-thiazol-4-yl]formamido}-2-methylpropanamido)-3-methylbutanoyl]oxy}pent-4-enoate수율 96%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(2-((tert-butoxycarbonylamino) methyl)thiazole-4-carboxamido)-2-methylpropanoic acid (1.26 g, 3.67 mmole) in 10 mL Dimethylformamide was added HBTU(O-Benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate) (1.67 g, 4.40 mmole) and diisopropylethylamine (2.0 mL, 11.0 mmole). The resulting reaction mixture was stirred at room temperature for 10 minutes. (S)-tert-butyl 3-((S)-2-amino-3-methylbutanoyloxy)pent-4-enoate (1.0 g, 3.67 mmole) was added, and the resulting mixture was stirred overnight. Water and EtOAc were added and the layers were separated. The aqueous layer was extracted with EtOAc, the combined organic layer was dried over Na2SO4 and concentrated. It was purified by column chromatography, eluted with 1:1 Hex/EtOAc to get the desired product (2.1 g, 96% yield).

후처리

  1. customThe resulting reaction mixture
  2. stirringthe resulting mixture was stirred overnight
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customIt was purified by column chromatography
  8. washeluted with 1:1 Hex/EtOAc

출처 및 근거

ORD 기록
ord-80a1665a38a44add99e050f07caebb27
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754050B2

반응 노트

불러오는 중…