Methanol → HCID 11501867, compound

HRID 970213Notes

Reaction equation

HRID 970213 reaction equation
[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

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11625436HCID 11625436, compound

Product 1

HCID 11501867HCID 11501867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-247ae6194b9c4fe7959dfd398c4158da
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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