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

HRID 2371312Notes

Reaction equation

HRID 2371312 reaction equation
C[O:2][C:3](=[O:34])[C@@H:4]([NH:10][C:11](=[O:33])[C@@H:12]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH:23]=[CH2:24])=[CH:16][CH:15]=1)[CH2:5][CH:6]([CH2:8]C)[CH3:7].[OH-].[Na+].CO>C1COCC1.O>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@H:12]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:11]([NH:10][C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:34])=[O:2])=[O:33])=[CH:19][CH:18]=1)[CH2:22][CH:23]=[CH2:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66847191(S)-2-[(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-ethyl-pentanoic acid methyl ester

Product 1

HCID 66847077(S)-2-[(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl ester 20 (2.30 g, 4.97 mmol) was dissolved in THF (30 mL) and NaOH (0.298 g, 7.46 mmol) dissolved in water (10 mL) was added. Methanol (10 mL) was added to obtain a homogenous solution and this was stirred at rt for 18 h. The reaction mixture was then concentrated in vacuo and 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 solid, 2.14 g, 96%. m.p. 68-70° C.

Workup

  1. additionwas added
  2. customto obtain a homogenous solution
  3. concentrationThe reaction mixture was then 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 solid, 2.14 g, 96%

Sources & evidence

ORD record
ord-80da88b58bed4aa58a8bc2985b1457bb
Source dataset
uspto-grants-2014_04
Patent number
US08710178B2

Reaction notes

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