Chloroacetyl chloride → methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate

HRID 475347

Reaction equation

HRID 475347 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[NH:11][C@H:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:8]1)([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>O1CCCC1>[Cl:23][CH2:24][C:25]([N:11]1[C@@H:7]([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:8][CH2:9][C@H:10]1[C:12]([O:14][CH3:15])=[O:13])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 16090847methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

Product 1

HCID 59683665methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate (2.76 g, 12.2 mmol) and triethylamine (2.13 mL, 15.3 mmol) in dry tetrahydrofuran (50 mL) at 0° C. was gradually added a solution of chloroacetyl chloride (0.97 mL, 12.2 mmol) in dry tetrahydrofuran (10 mL). After stirring at room temperature for 2 hours, the mixture was filtered. The solid cake was washed with THF, and the filtrate and washings were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue taken up in toluene and concentrated to dryness under reduced pressure to provide the titled compound. MS (CI) m/z 302 (M+1)+.

Workup

  1. filtrationthe mixture was filtered
  2. washThe solid cake was washed with THF
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-944831aa6df2418785d642acb79650d5
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Linked notes

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