Chloroacetyl chloride → methyl (3S)-1-(chloroacetyl)-3-hydroxy-L-prolinate

HRID 2074858Notes

Reaction equation

HRID 2074858 reaction equation
Cl.[OH:2][C@H:3]1[CH2:7][CH2:6][NH:5][C@@H:4]1[C:8]([O:10][CH3:11])=[O:9].CCN(CC)CC.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C1C=CC=CC=1>[Cl:19][CH2:20][C:21]([N:5]1[CH2:6][CH2:7][C@H:3]([OH:2])[C@H:4]1[C:8]([O:10][CH3:11])=[O:9])=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66605223methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 59215866methyl (3S)-1-(chloroacetyl)-3-hydroxy-L-prolinateYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of the methyl (3S)-3-hydroxy-L-prolinate hydrochloride (D68, 1.8 g, 9.9 mmol) and Et3N (3 ml, 21.8 mmol) in 10 ml of dry benzene at the temperature of 7-8° C. was added dropwise a solution of chloroacetyl chloride (0.87 ml, 10.9 mmol) in 5 ml of dry benzene. After 24 h at rt, the precipitated was filtered off and washed with AcOEt. The filtrate was evaporated, and the crude oil was purified by flash chromatography column (Cy/AcOEt 1/4 as eluent). The title compound was isolated as a colourless oil (1.48 g). Yield 67%.

Workup

  1. filtrationthe precipitated was filtered off
  2. washwashed with AcOEt
  3. customThe filtrate was evaporated
  4. customthe crude oil was purified by flash chromatography column (Cy/AcOEt 1/4 as eluent)

Sources & evidence

ORD record
ord-aee5bab76e494c9cb053424ff7f78726
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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