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

HRID 58376Notes

Reaction equation

HRID 58376 reaction equation
C[O:2][C:3](=[O:31])[C@@H:4]([NH:8][C:9](=[O:30])[C@@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]=[CH2:21])=[CH:14][CH:13]=1)[CH:5]([CH3:7])[CH3:6].[OH-].[Na+].CO>C1COCC1.O>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C:9]([NH:8][C@@H:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:31])=[O:2])=[O:30])=[CH:13][CH:14]=1)[CH:20]=[CH2:21]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14632374(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

Product 1

HCID 66847200(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl ester 42 (4.90 g, 11.3 mmol) was dissolved in THF (35 mL) and sodium hydroxide (17 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, 4.60 g, 97%.

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, 4.60 g, 97%

Sources & evidence

ORD record
ord-af33676ac0ae4b04b273ccfb47088607
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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