Acetic Anhydride → HCID 71245349, compound

HRID 1186021Notes

Reaction equation

HRID 1186021 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[CH:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]([OH:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24](OC(C)=O)=[O:25].CCN(CC)CC>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:22])[CH:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]([O:13][C:24](=[O:25])[CH3:23])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13967208HCID 13967208, compound

Product 1

HCID 71245349HCID 71245349, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of benzyl-2-(tert-butoxycarbonylamino)-3-hydroxybutanoate (2.8 g, 9.06 mmol) in THF (80 mL) was added Ac2O (1.1 g, 10.87 mmol), Et3N (1.51 mL, 10.87 mmol) and DMAP (280 mg) and stirred at RT for 15 min. The volatiles were removed under reduced pressure. The residue obtained was diluted with EtOAc (150 mL) and washed with cold 0.5N HCl solution (2×20 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 3-acetoxy-2-(tert-butoxycarbonylamino)-butanoate 11 (2.8 g, 88%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue obtained
  3. washwashed with cold 0.5N HCl solution (2×20 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5b6e1c9d18a49d0a11d3326eb05baf2
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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