1,2-Dichloroethane → 2-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate

HRID 1776559Notes

Reaction equation

HRID 1776559 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3].O[CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(Cl)CCl>C(Cl)Cl.C(Cl)Cl.CO.CN(C1C=CN=CC=1)C>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 15066094-{[(Methylsulfonyl)amino]methyl}benzoic acid

Product 1

HCID 866795152-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoateYield 60.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4-(methylsulfonamidomethyl)benzoic acid (0.4 g, 1.745 mmol) and benzyl 2-hydroxyacetate (0.290 g, 1.745 mmol) in a mixture of DCM and THF 1/1 (50 ml), EDC (0.334 g, 1.745 mmol) and DMAP (0.256 g, 2.094 mmol) were added in one portion. The reaction was stirred at RT for 3 hours. The solvent was removed under vacuum and the resulting crude was portioned between EtOAc and HCl 2N. The organic phase was separated, washed with brine and dried over Na2SO4. The solvent was removed under vacuum affording 2-(benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate (0.4 g, 1.060 mmol, 60.7% yield, MS/ESI+ 377.9 [MH]+). This product was employed in the following step without any further purification.

Workup

  1. additionwere added in one portion
  2. customThe solvent was removed under vacuum
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ac348c8047d345f4a89be2d61033404a
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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