Lithium Hydroxide → 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid

HRID 1701071Notes

Reaction equation

HRID 1701071 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].[OH-].[Li+]>C(O)C>[C:32]([O:31][C:29]([NH:28][C@@H:16]([C:7]1[S:8][C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 541387142-((1R)-1-(tert-Butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid methylester

Product 1

HCID 541039172-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acidYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-((1R)-1-(tert-Butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid methylester (0.35 g; 0.716 mmol) was dissolved in ethanol (99%; 40 ml) and lithium hydroxide (0.112 g; 4.654 mmol) was added. The reaction mixture was stirred 12 hours at room temperature. The solvent was removed in vacuo and the residue was dissolved in water (50 ml) and diethyl ether (50 ml). The solution was made acidic with sodium hydrogensulfate (10%), and the organic phase was dried (magnesium sulfate). The solvent was removed in vacuo to afford 0.185 g of 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. dry with materialthe organic phase was dried (magnesium sulfate)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-170b764bc12d45a09ae908f9c8236722
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

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