Sodium Hydroxide → Glpg-0974

HRID 408626노트

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HRID 408626 반응식
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][N:7]([C:16]([C@@:18]1([CH3:33])[CH2:21][CH2:20][N:19]1[C:22]([C:24]1[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[S:27][CH:28]=1)=[O:23])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1.[OH-].[Na+]>CO>[S:27]1[CH:28]=[C:24]([C:22]([N:19]2[CH2:20][CH2:21][C@:18]2([CH3:33])[C:16]([N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH2:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:17])=[O:23])[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]1=2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 705573284-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester

생성물 1

HCID 57520598Glpg-0974수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

To a solution of 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester, Intermediate 112 (25 g, 1 eq.) in 750 mL of MeOH was added aqueous NaOH (2N) (75 mL, 3 eq.). The reaction was stirred at 20° C. for 15 h. The solvent was removed under reduced pressure and the crude was partitioned between water and EtOAc. The organic layer was discarded. The aqueous layer was acidified by addition of HCl (2N) until pH=2 and thoroughly extracted three times with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid (23.7 g, yield=97%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between water and EtOAc
  3. additionThe aqueous layer was acidified by addition of HCl (2N) until pH=2
  4. extractionthoroughly extracted three times with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3e7fbe8451e243f8ab8ca292f3528aed
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759334B2

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