Sodium Bicarbonate → N-(5-Chlorothiophene-2-carbonyl)-2-(methoxymethyl)-O-methylserine

HRID 2174714Notes

Reaction equation

HRID 2174714 reaction equation
[OH:1][CH2:2][C:3]([NH:10][C:11]([C:13]1[S:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:12])([CH2:7][O:8][CH3:9])[CH2:4][O:5][CH3:6].C(=O)([O-])[OH:20].[Na+].Cl[O-].[Na+]>O>[Cl:18][C:15]1[S:14][C:13]([C:11]([NH:10][C:3]([CH2:4][O:5][CH3:6])([CH2:7][O:8][CH3:9])[C:2]([OH:20])=[O:1])=[O:12])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 68486309HCID 68486309, compound

Product 1

HCID 67456065N-(5-Chlorothiophene-2-carbonyl)-2-(methoxymethyl)-O-methylserine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.20 g (0.49 mmol) 5-chloro-thiophene-2-carboxylic acid(1-hydroxymethyl-2-methoxy-1-methoxymethyl-ethyl)-amide are dissolved at room temperature in 3 ml of water/3 ml acetonitrile and combined with 0.08 g (0.51 mmol) 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO) and 0.13 g (1.55 mmol) sodium hydrogen carbonate. Then 1.5 ml (3.14 mmol) of 13% sodium hypochlorite is added dropwise and the mixture is stirred for 2 h. The reaction mixture is concentrated by evaporation i.vac. And purified by chromatography through RP material (Microsorb C18 Varian; eluant: water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation i.vac
  2. customAnd purified by chromatography through RP material (Microsorb C18 Varian; eluant: water/acetonitrile/trifluoroacetic acid=90:10:0.1=>0:100:0.1)

Sources & evidence

ORD record
ord-2230b5e1016443079ba03a9183600b4e
Source dataset
uspto-grants-2015_06
Patent number
US09062034B2

Reaction notes

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