Methanol → HCID 66846978, compound

HRID 58363Notes

Reaction equation

HRID 58363 reaction equation
C[O:2][C:3](=[O:35])[C@@H:4]([NH:9][C:10](=[O:34])[C@@H:11]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)(=[O:26])=[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][S:24]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[C:10]([NH:9][C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:35])=[O:2])=[O:34])=[CH:14][CH:15]=1)[CH:21]=[CH2:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66847193(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-(4-fluoro-benzenesulfonylamino)-propionylamino]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 66846978HCID 66846978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl ester 11 (2.70 g, 5.33 mmol) was dissolved in THF (30 mL). Sodium hydroxide (0.853 g, 21.3 mmol) pre-dissolved in water (10 mL) was added. Methanol (15 mL) was added to obtain a homogenous solution and this 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, 2.50 g, 95%.

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, 2.50 g, 95%

Sources & evidence

ORD record
ord-e648fa33891e4551b38771f3b37859ed
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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