Hydrochloric Acid → HCID 69426539, compound

HRID 970818Notes

Reaction equation

HRID 970818 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:22][C:21]=2[CH:31]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Li+].Cl>O1CCOCC1.O>[C:25]1([C:23]2[O:24][C:20]3[CH:19]=[CH: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:31][C:21]=3[N:22]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 12990928HCID 12990928, compound

Product 1

HCID 69426539HCID 69426539, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution (R)-2-(2-phenylbenzoxazol-5-ylmethoxycarbonylamino)-3-phenylpropionic acid methyl ester 59 (374 mg, 0.8 mmol) in dioxane (8 ml) was treated with a solution of lithium hydroxide hydrate (55 mg, 1.3 mmol) in water (4 mL) under an atmosphere of N2 and stirred for 3 hrs at room temperature. The mixture was acidified with 1N HCl, then extracted with ethyl acetate (25 ml). The ethyl acetate extract was washed, and dried. Evaporation of the solvent afforded the product which was recrystallized to yield 220 mg (60%) of (R)-2-(2-phenylbenzoxazol-5-ylmethoxycarbonylamino)-3-phenyl propionic acid 60, mp. 220.0-221.4° C.

Workup

  1. extractionextracted with ethyl acetate (25 ml)
  2. extractionThe ethyl acetate extract
  3. washwas washed
  4. customdried
  5. customEvaporation of the solvent
  6. customafforded the product which
  7. customwas recrystallized

Sources & evidence

ORD record
ord-854977a8459e44298531283473d756c6
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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