1,2-Dichloroethane → HCID 86679499, compound

HRID 1776543Notes

Reaction equation

HRID 1776543 reaction equation
[NH2:1][C:2](=[O:20])[CH2:3][N:4]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:12]([OH:14])=[O:13])[S:5]([CH3:8])(=[O:7])=[O:6].O[CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:1][C:2](=[O:20])[CH2:3][N:4]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:12]([O:14][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:13])[S:5]([CH3:8])(=[O:7])=[O:6]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 86679498HCID 86679498, compound

Product 1

HCID 86679499HCID 86679499, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(N-(2-amino-2-oxoethyl)methylsulfonamido)-4-methoxybenzoic acid (150 mg, 0.496 mmol), benzyl 2-hydroxyacetate (165 mg, 0.992 mmol), DMAP (121 mg, 0.992 mmol), and EDC (285 mg, 1.489 mmol) were dissolved in DMF (2 ml). The reaction was stirred at RT for 3 h to achieve completion. The reaction mixture was diluted with water, and extracted with EtOAc. The organic phase was washed with HCl 1N, Na2CO3 sat. sol. and brine, dried over Na2SO4 and concentrated under vacuum to give 2-(benzyloxy)-2-oxoethyl 3-(N-(2-amino-2-oxoethyl)-methylsulfonamido)-4-methoxybenzoate (180 mg, 81% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with HCl 1N, Na2CO3 sat. sol. and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-882cfa363c0041efb13a69dfa6b8f51f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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