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

HRID 849885Notes

Reaction equation

HRID 849885 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-432986ed14e84fc09b10a056d341fc16
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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