Hydrochloric Acid → (R)-2-(5-thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenylpropionic acid

HRID 970797Notes

Reaction equation

HRID 970797 reaction equation
C[O:2][C:3](=[O:31])[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:30]=[CH:29][S: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>[S:28]1[CH:29]=[CH:30][C:26]([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:31])=[O:2])=[O:14])=[CH:21][C:20]=3[CH:22]=2)=[CH:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 12990913(R)-2-(5-Thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester

Product 1

HCID 12990914(R)-2-(5-thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenylpropionic acidYield 65.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-2-(5-thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenyl-propionic acid methyl ester 23 (0.23 g, 0.54 mmole) in methanol (10 ml) was treated with a solution of lithium hydroxide monohydrate (25 mg, 0.59 mmole) in water (1 ml) and heated to 50° C. for 4 hrs, cooled, acidified with 1M HCl, evaporated, partitioned between ethyl acetate and 1M HCl, separated, washed, dried, and evaporated. The residue was crystallized giving about 0.15 g of (R)-2-(5-thiophen-3-yl-benzofuran-2-ylmethoxycarbonylamino)-3-phenylpropionic acid 24, mp. 169-170° C.

Workup

  1. temperaturecooled
  2. customevaporated
  3. custompartitioned between ethyl acetate and 1M HCl
  4. customseparated
  5. washwashed
  6. customdried
  7. customevaporated
  8. customThe residue was crystallized

Sources & evidence

ORD record
ord-52550bbb011d44329151379997756e6a
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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