Chloroacetyl chloride → (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid

HRID 249886Notes

Reaction equation

HRID 249886 reaction equation
Cl.[CH2:2]([NH:9][C@H:10]([CH2:14][OH:15])[C:11]([OH:13])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:18][CH2:19][C:20](Cl)=[O:21]>O>[CH2:2]([N:9]([C@H:10]([CH2:14][OH:15])[C:11]([OH:13])=[O:12])[C:20](=[O:21])[CH2:19][Cl:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 66875097(R)-2-(benzylamino)-3-hydroxypropanoic acid hydrochloride

Product 1

HCID 13543368(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acidYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (R)-2-(benzylamino)-3-hydroxypropanoic acid hydrochloride (9.4 g, 48.2 mmol) and sodium hydroxide (2.57 g, 82.9 mmol) in H2O (30 mL) at 0° C. was added drop wise chloroacetyl chloride (4.9 mL, 62.1 mL) while maintaining the temperature below 10° C. The reaction mixture was then warmed to room temperature and stirred for 2 hours. The reaction mixture was extracted with CH2Cl2 (2×250 mL) and the organic layer dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid) to provide (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid (2.6 g, 20%) as a yellow foam. 1H NMR consistent.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. extractionThe reaction mixture was extracted with CH2Cl2 (2×250 mL)
  3. dry with materialthe organic layer dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid)

Sources & evidence

ORD record
ord-755e1e78f7d1449eb2e2331ec57b83f4
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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