Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionate → (2R)-2-Benzyl-3-thiazol-4-ylpropionic Acid

HRID 973502Notes

Reaction equation

HRID 973502 reaction equation
[CH2:1]([C@H:8]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)[C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br.C(O)(=O)C>[CH2:1]([C@H:8]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15018104Benzyl (2R)-2-Benzyl-3-thiazol-4-ylpropionate

Product 1

HCID 15018105(2R)-2-Benzyl-3-thiazol-4-ylpropionic AcidYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

The resultant compound from Example 35 (364 mg) was stirred for 2 h in 30% HBr in acetic acid (5 ml). The solvent was evaporated and the residue was dissolved in 1M HCl and washed with ether. The aqueous phase was adjusted to pH 4 with solid NaHCO3 and extracted with chloroform which was dried over Na2SO4 and evaporated to afford 186.5 mg (70%) of an oil. 1H NMR (CDCl3) δ8.78 (d,1H), 7.15-7.35 (m,5H), 6.99 (d,1H), 3.00-3.30 (m,4H), 2.81 (dd,1H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 1M HCl
  3. washwashed with ether
  4. extractionextracted with chloroform which
  5. dry with materialwas dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-f846b86695074c359e9dcd8cd86e6d4a
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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