Acetic Anhydride → HCID 86686080, compound

HRID 239177Notes

Reaction equation

HRID 239177 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH:22]([OH:25])[CH:21]([NH2:26])[CH2:20][CH:19]1CC1C=CC=CC=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH:22]([OH:25])[CH:21]([NH:26][C:1](=[O:3])[CH3:2])[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 86686081Benzyl 4-amino-5-hydroxy-azepane-1-carboxylic acid benzyl ester

Product 1

HCID 86686080HCID 86686080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 mL acetic anhydride was added to 8.4 g benzyl 4-amino-5-hydroxy-azepane-1-carboxylic acid benzyl ester in 115 ml dichloromethane at 0° C. After 1 h at RT, saturated sodium bicarbonate was added. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phase was washed with brine, dried over sodium sulphate, filtered and concentrated. The residue was purified by chromatographie on silica gel (ethyl acetate/hexane 2:1) to yield 4.5 g of the desired product. (M+H)+: 307

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatographie on silica gel (ethyl acetate/hexane 2:1)

Sources & evidence

ORD record
ord-6c5db16dab3b44c68f261948dac85555
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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