Sodium Hydroxide → Glpg-0974

HRID 408626ノート

反応式

HRID 408626 の反応式
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

参加物

4

反応物 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

生成物 1

HCID 57520598Glpg-0974収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3e7fbe8451e243f8ab8ca292f3528aed
出典データセット
uspto-grants-2014_06
特許番号
US08759334B2

反応ノート

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