Sodium Hydroxide → HCID 11441991, compound

HRID 1994073Notes

Reaction equation

HRID 1994073 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH:15]=1)=[O:12])=[O:5])C.[OH-].[Na+]>CO.O>[CH3:27][C:26]1[O:25][C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:23][C:22]=1[CH2:21][O:20][C:16]1[CH:15]=[C:14]([S:13][C:11]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86605610HCID 86605610, compound

Product 1

HCID 11441991HCID 11441991, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the title D compound, (R)-1-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenylsulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester (1.5 g, 3.22 mmol) in methanol (15 mL) is added sodium hydroxide (0.26 g, 6.44 mmol) in water (10 mL) at RT. The reaction mixture is stirred for 4 h. The reaction mixture is concentrated at reduced pressure, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is concentrated and triturated with 1:1 methyl-t-butyl ether and hexane to give (R)-1-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenylsulfanylcarbonyl]-pyrrolidine-2-carboxylic acid as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated at reduced pressure
  2. additionpoured into water
  3. customthe aqueous layer is separated
  4. washwashed with ethyl acetate twice
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined ethyl acetate extract
  7. concentrationis concentrated
  8. customtriturated with 1:1 methyl-t-butyl ether and hexane

Sources & evidence

ORD record
ord-0e800c9e11c84354aa0abb2b64c9ecc8
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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