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Hydrochloric Acid → Aminothiazole, 22

HRID 1816176
Notes
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Reaction equation

HRID 1816176 reaction equation
C[O:2][C:3](=[O:43])[C@H:4]([OH:42])[CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[CH2:37][CH2:36][CH2:35]3)[C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:20]=2)=[CH:10][CH:9]=1.[OH-].[Na+].Cl.O>CO>[OH:42][C@H:4]([CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[CH2:37][CH2:36][CH2:35]3)[C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:29])[F:31])=[CH:25][CH:26]=3)[N:20]=2)=[CH:10][CH:9]=1)[C:3]([OH:43])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 426376622(R)-Hydroxy-3-[4-({indan-5-yl-[4-(4-trifluoromethoxyphenyl)thiazol-2-yl]amino}methyl)-benzoylamino]propionic acid methyl ester

Product 1

HCID 20775791Aminothiazole, 22

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

2(R)-Hydroxy-3-[4-({indan-5-yl-[4-(4-trifluoromethoxyphenyl)thiazol-2-yl]amino}methyl)benzoylamino]propionic acid methyl ester (0.10 g, 0.16 mmol) was dissolved in methanol (5 mL) and 1 N aqueous sodium hydroxide (0.16 mL, 0.16 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. 1 N hydrochloric acid (0.17 mL) and water (50 mL) were added and the mixture was extracted with ethyl acetate (50 mL). The organic phase was washed with water (50 mL), dried (MgSO4) and concentrated in vacuo. This afforded 0.06 g (61%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic phase was washed with water (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-988303884a3f4a328a5ace4be964645b
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06881746B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes