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 1485847ノート

反応式

HRID 1485847 の反応式
[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]

参加物

7

反応物 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

生成物 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-enoate収率 96%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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. (5)-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).

後処理

  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

出典と根拠

ORDレコード
ord-ada3e7d5e2d14864896057bcb97ecd20
出典データセット
uspto-grants-2016_08
特許番号
US09422340B2

反応ノート

読み込み中…