1,2-Dichloroethane → HCID 89455858, compound

HRID 1776534Notes

Reaction equation

HRID 1776534 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(Cl)CCl.[C:17]([O:21][C:22]([N:24]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[C:32](O)=[O:33])[S:25]([CH3:28])(=[O:27])=[O:26])=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17]([O:21][C:22]([N:24]([C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[C:32]([O:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:33])[S:25]([CH3:28])(=[O:27])=[O:26])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 89455725HCID 89455725, compound

Product 1

HCID 89455858HCID 89455858, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-hydroxyacetate (0.234 g, 1.410 mmol), EDC (0.541 g, 2.82 mmol) and DMAP (0.086 g, 0.705 mmol) in DCM (25 ml), 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoic acid (0.487 g, 1.410 mmol) was added, and the reaction was stirred at RT for 1 hour. The mixture was washed with HCl 1N and with NaHCO3 5%; the organic phase was dried over Na2SO4, and the solvent was removed. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 70:30) to give 2-(benzyloxy)-2-oxoethyl 3-(N-(tert-butoxycarbonyl)-methylsulfonamido)-4-methoxybenzoate (0.508 g, 1.029 mmol, 73.0% yield, MS/ESI+ 515.9 [MNa]+).

Workup

  1. washThe mixture was washed with HCl 1N and with NaHCO3 5%
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customthe solvent was removed
  4. customThe crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 70:30)

Sources & evidence

ORD record
ord-9c953b155c1a48eba14eec0ba897d593
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…