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Citric Acid → (S)-2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

HRID 447160
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HRID 447160 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:31][C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([O:29]C)=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:31][C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 67236274HCID 67236274, 화합물

생성물 1

HCID 67236426(S)-2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

(S)-methyl 2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate (0.61 g, 1.15 mmol) was dissolved in methanol (6 ml) followed by the addition of 1N NaOH (1.26 ml, 1.26 mmol) and the resulting mixture heated to 50° C. overnight. The resulting mixture was then cooled to room temperature, acidified with 10% citric acid and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated in vacuo to yield (S)-2-(4-(2-(tert-butoxycarbonylamino)-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid.

후처리

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2aff118c6ab74071a4b4aa1fb11daf23
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481547B2

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