Ethyl Acetate → HCID 53890669, compound

HRID 617613Notes

Reaction equation

HRID 617613 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:20][CH3:21])[CH2:18][OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](OCC)(=[O:32])[CH3:31]>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:30]([O:19][CH2:18][C:17]([NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])([CH2:20][CH3:21])[CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22618752HCID 22618752, compound

Product 1

HCID 53890669HCID 53890669, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-(4-benzyloxyphenyl)-2-tert-butoxycarbonylamino-2-ethylbutanol (24 g) in pyridine (200 ml) and acetic anhydride (32 ml) was allowed to stand at room temperature overnight. Ethyl acetate was added to the reaction mixture and the mixture was washed with water, a dilute hydrochloric acid, an aqueous sodium hydrogencarbonate solution and a saturated brine in order, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1) to give the subject compound (13 g).

Workup

  1. washthe mixture was washed with water
  2. dry with materiala dilute hydrochloric acid, an aqueous sodium hydrogencarbonate solution and a saturated brine in order, and dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-0e582ea9ae994c14b4e3b7c2c8555830
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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