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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
Notes
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Reaction equation

HRID 447160 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-2aff118c6ab74071a4b4aa1fb11daf23
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481547B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes