Acetic Anhydride → (2S)-acetic acid 6-tert-butoxycarbonylamino-2-[(4-tert-butoxycarbonylamino-benzenesulfonyl)-isobutyl-amino]-hexyl ester

HRID 132702Notes

Reaction equation

HRID 132702 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](=[O:36])(=[O:35])[N:15]([C@H:20]([CH2:33][OH:34])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:38](OC(=O)C)(=[O:40])[CH3:39]>C(Cl)Cl>[C:29]([O:28][C:26]([NH:25][CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]([N:15]([S:14]([C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:37])=[CH:13][CH:12]=1)(=[O:36])=[O:35])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:33][O:34][C:38](=[O:40])[CH3:39])=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59733922(1S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 131726926(2S)-acetic acid 6-tert-butoxycarbonylamino-2-[(4-tert-butoxycarbonylamino-benzenesulfonyl)-isobutyl-amino]-hexyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester (intermediate product (VII) of example 1, step D, 97 mg, 0.18 mmol) in anhydrous CH2Cl2 (3 mL) was added N,N-dimethylaminopyridine (22 mg, 0.18 mmol) and acetic anhydride (0.014 mL, 0.18 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was evaporated. Ethyl acetate (50 mL) was added and the organic layer was washed with water (30 mL), then dried with Na2SO4 and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate. The yield obtained was quantitative (100 mg).

Workup

  1. customThe solvent was evaporated
  2. additionEthyl acetate (50 mL) was added
  3. washthe organic layer was washed with water (30 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate
  8. customThe yield obtained

Sources & evidence

ORD record
ord-12b49c1426fe461388a0e6238610c8d7
Source dataset
uspto-grants-2008_06
Patent number
US07388008B2

Reaction notes

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