Methanol → (S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid

HRID 2371302Notes

Reaction equation

HRID 2371302 reaction equation
C[O:2][C:3](=[O:32])[C@@H:4]([NH:9][C:10](=[O:31])[C@@H:11]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]=[CH2:22])=[CH:15][CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[OH-].[Na+].CO>C1COCC1.O>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C@H:11]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:10]([NH:9][C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:32])=[O:2])=[O:31])=[CH:14][CH:15]=1)[CH:21]=[CH2:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86650238(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 66847292(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl ester 1 (8.45 g, 18.8 mmol) was dissolved in THF (35 mL) and sodium hydroxide (1.13 g, 28.2 mmol) pre-dissolved in water (10 mL) was added. A further 15 mL of THF and 20 mL of methanol were added to obtain a homogenous solution. The reaction mixture was stirred at rt for 18 h before being concentrated in vacuo. The residue was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted twice more with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to yield a white foam, 7.25 g, 89%.

Workup

  1. additionwas added
  2. customto obtain a homogenous solution
  3. concentrationbefore being concentrated in vacuo
  4. customThe residue was partitioned between EtOAc and 1M hydrochloric acid
  5. extractionThe aqueous phase was extracted twice more with EtOAc
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a white foam, 7.25 g, 89%

Sources & evidence

ORD record
ord-591d09a5f5af45109d4b0034aa7585d1
Source dataset
uspto-grants-2014_04
Patent number
US08710178B2

Reaction notes

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