Hydrochloric Acid → (2S)-2-{(S)-[(4-bromophenyl)thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid

HRID 2223575Notes

Reaction equation

HRID 2223575 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:14][CH:15]([C:20]23OCC(C)(C[O:25]2)C[O:21]3)[CH2:16][CH:17]([CH3:19])[CH3:18])[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.Cl>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:14][C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:20]([OH:25])=[O:21])[C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67298665[(4-Bromo-phenyl)-thiazol-2-yl-methyl]-[3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-amine

Product 1

HCID 67298316(2S)-2-{(S)-[(4-bromophenyl)thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(4-bromo-phenyl)-thiazol-2-yl-methyl]-[3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-amine (500 mg, 1.06 mmol) in THF (20 mL) and water (18 mL), was added 1N HCl (3.5 mL). The reaction mixture was stirred for 2 h. After checking the TLC for the disapperance of the starting material, Li(OH).H2O (280.2 mg, 6.3 eq.) was added and stirred at room temperature for 2 h. Then 1N HCl was added to adjust the pH 4-6, and the product was extracted with EtOAC and the organic layer dried over MgSO4. The solvent was evaporated to yield (2S)-2-{(S)-[(4-bromophenyl)-thiazol-2-yl-methyl]-amino}-4-methylpentanoic acid as a yellow solid.

Workup

  1. stirringstirred at room temperature for 2 h
  2. extractionthe product was extracted with EtOAC
  3. dry with materialthe organic layer dried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-48bacb348b4b48d7abd50d3e5028c624
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

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