Benzenesulfonyl chloride → 4-Benzyloxy-3-(phenylsulphonylamino)phenyl acetate

HRID 28388Notes

Reaction equation

HRID 28388 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH2:19])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH:19][S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 100153213-Amino-4-benzyloxyphenyl acetate

Product 1

HCID 544537464-Benzyloxy-3-(phenylsulphonylamino)phenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.0 g (0.0194 mol) of 4-benzyloxy-3-aminophenyl acetate, 3.3 ml (0.0236 mol) of triethylamine and 3.0 ml (0.0236 mol) of benzenesulphonyl chloride in 150 ml of methylene chloride is stirred at room temperature overnight. The mixture is then washed with water and the organic phase is dried, followed by purification by chromatography on a silica gel column, eluting with a 7/3 cyclohexane/ethyl acetate mixture. The compound of the title is obtained.

Workup

  1. washThe mixture is then washed with water
  2. customthe organic phase is dried
  3. customfollowed by purification by chromatography on a silica gel column
  4. washeluting with a 7/3 cyclohexane/ethyl acetate mixture
  5. customThe compound of the title is obtained

Sources & evidence

ORD record
ord-40eb032d716e4c5bbe51acdd460f469d
Source dataset
uspto-grants-2008_09
Patent number
US07419974B2

Reaction notes

Loading…