1,2-Dichloroethane → HCID 86679535, compound

HRID 1776582Notes

Reaction equation

HRID 1776582 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6]([O:8][C:9]1[CH:17]=[CH:16][C:15]([N:18]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:10]=1[C:11]([O:13][CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 86679534HCID 86679534, compound

Product 1

HCID 86679535HCID 86679535, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)-methylsulfonamido)benzoic acid (0.300 g, 0.778 mmol), benzyl 2-hydroxyacetate (0.129 g, 0.778 mmol), EDC (0.448 g, 2.335 mmol) and DMAP (0.048 g, 0.389 mmol) in DCM (30 ml) was stirred at RT overnight. The reaction mixture was washed twice with HCl 1N and then with NaHCO3 5%. The organic phase was dried over Na2SO4, and the solvent was removed under vacuum. The crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20 to 70:30) to give 2-(benzyloxy)-2-oxoethyl 2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)methylsulfonamido)benzoate (0.288 g, 0.540 mmol, 69.3% yield, MS/ESI+ 555.96 [MNa]+).

Workup

  1. washThe reaction mixture was washed twice with HCl 1N
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed under vacuum
  4. filtrationThe crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20 to 70:30)

Sources & evidence

ORD record
ord-34dbcf7b7172403190ad6c6dd8d00050
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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