Methanol → HCID 11501867, 화합물

HRID 970213노트

반응식

HRID 970213 반응식
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C@H:6](/[CH:20]=[CH:21]/[CH3:22])[C@@H:7]([C:16]([O:18]C)=[O:17])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C@H:6](/[CH:20]=[CH:21]/[CH3:22])[C@@H:7]([C:16]([OH:18])=[O:17])[NH:8][C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11625436HCID 11625436, 화합물

생성물 1

HCID 11501867HCID 11501867, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 25 g (62.8 mmol) of methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate (Step D) in 600 mL of tetrahydrofuran (THF) was added in succession 200 mL of methanol and 200 mL (200 mmol) of 1N aqueous sodium hydroxide solution. The reaction mixture was stirred at ambient temperature for 3 h, and then the methanol and THF were removed under reduced pressure. To the aqueous mixture was added 250 mL of 1N hydrochloric acid and the mixture was extracted with ethyl acetate (3×300 mL). The combined organic extracts were washed with brine (300 mL) then dried over sodium sulfate, filtered, and concentrated in vacuo to afford the carboxylic acid, which was used without further purification.

후처리

  1. customthe methanol and THF were removed under reduced pressure
  2. additionTo the aqueous mixture was added 250 mL of 1N hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate (3×300 mL)
  4. washThe combined organic extracts were washed with brine (300 mL)
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-247ae6194b9c4fe7959dfd398c4158da
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07309714B2

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