Sodium Hydroxide → (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid

HRID 1994079

반응식

HRID 1994079 반응식
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:35])[C:12]([CH3:34])([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)[CH3:13])=[O:5])C.[OH-].[Na+]>CO.O>[CH3:34][C:12]([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)([CH3:13])[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:35]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 68675740(R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester

생성물 1

HCID 11362875(R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a stirred solution of title D compound, (R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester (0.47 g, 0.99 mmol) in methanol (25 mL) is added sodium hydroxide (0.16 g, 3.95 mmol) in water (5 mL) at RT. The reaction mixture is stirred for 16 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 dried and concentrated to give (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid as a white solid: MS m/z 447.3 [M−1]−.

후처리

  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. customis dried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7f9b55db6907457499864929752d2d34
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652061B2

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