Water → HCID 68513181, compound

HRID 1877078Notes

Reaction equation

HRID 1877078 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:9])[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27])([O-:19])=[O:18].O>CN(C)C=O>[OH:9][CH:4]([CH2:3][NH:2][S:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N+:17]([O-:19])=[O:18])(=[O:27])=[O:28])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 71757671Methyl 3-amino-2-hydroxypropanoate hydrochloride

Product 1

HCID 68513181HCID 68513181, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-amino-2-hydroxypropanoate hydrochloride (0.8 g) in N,N-dimethylformamide (10 mL) were added triethylamine (1.1 mL) and 2-nitrobenzenesulfonyl chloride (1.1 g) at 0° C., and the mixture was stirred at 0° C. for 2 hr and then at room temperature overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.1 g, 89%) as an oil.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b114ac518e041c79ad53fd1fd61d2a1
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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