Acetic Anhydride → HCID 86599587, compound

HRID 1174396Notes

Reaction equation

HRID 1174396 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([O:17]CC1C=CC=CC=1)=[O:16])[C:10]([CH3:14])([CH2:12][OH:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>ClCCl.CN(C)C1C=CN=CC=1>[C:25]([O:13][CH2:12][C:10]([CH3:11])([CH3:14])[C@@H:9]([C:15]([OH:17])=[O:16])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67407089(S)-benzyl 2-(tert-butoxycarbonylamino)-4-hydroxy-3,3-dimethylbutanoate

Product 1

HCID 86599587HCID 86599587, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 174D (0.175 g, 0.519 mmol) in dichloromethane (5.0 mL) were added 4-(dimethylamino)pyridine (0.070 g, 0.573 mmol) and acetic anhydride (0.054 mL, 0.571 mmol) and the mixture was stirred at room temperature for 30 minutes. The reaction was extracted with ethyl acetate and the organic layer was washed with 10% citric acid, dilute NaHCO3, and brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in a mixture of ethyl acetate (4.0 mL) and methanol (1.0 mL) and 20% Pd(OH)2 on carbon (0.10 g) was added, and the reaction was stirred under an atmosphere of hydrogen (balloon pressure) for 1 hour. The mixture was filtered through celite and the solvent was evaporated to give the title compound (0.15 g), which was used without further purification.

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic layer was washed with 10% citric acid, dilute NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in a mixture of ethyl acetate (4.0 mL) and methanol (1.0 mL) and 20% Pd(OH)2 on carbon (0.10 g)
  7. additionwas added
  8. stirringthe reaction was stirred under an atmosphere of hydrogen (balloon pressure) for 1 hour
  9. filtrationThe mixture was filtered through celite
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c4d58a63d0d847eca67771b24ef7b08d
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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