Hydrochloric Acid → (R)-2-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic Acid

HRID 970793Notes

Reaction equation

HRID 970793 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][C:20]=2[CH:21]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Li+].Cl>CO.O>[C:26]1([C:23]2[CH:24]=[CH:25][C:19]3[O:18][C:17]([CH2:16][O:15][C:13]([NH:12][C@H:4]([CH2:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:3]([OH:32])=[O:2])=[O:14])=[CH:21][C:20]=3[CH:22]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 12990909(R)-2-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-3-phenylpropionic Acid Methyl Ester

Product 1

HCID 11223758(R)-2-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic AcidYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid methyl ester 18 (1.39 g, 3.24 mmole) in methanol (30 ml) was treated with a solution of lithium hydroxide monohydrate (149 mg, 3.56 mmole) in water (2 ml) and heated to 50° C. for 3 hrs. It was then cooled to room temperature, acidified with 1M HCl, extracted with ethyl acetate, separated, washed, dried, and evaporated. The residue was crystallized to give about 1.13 g of (R)-2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid 19, mp. 154-156° C.

Workup

  1. temperatureIt was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. customseparated
  4. washwashed
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized

Sources & evidence

ORD record
ord-2f5f06430d39497d96a37cdbd4052c68
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

Loading…