Chloroacetyl chloride → HCID 66756837, compound

HRID 475403Notes

Reaction equation

HRID 475403 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([O-:5])=[O:4].[CH2:9](N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19].O1C[CH2:24][CH2:23][CH2:22]1>>[Cl:16][CH2:17][C:18]([N:1]1[C@@H:8]([C:22]#[C:23][CH3:24])[CH2:7][CH2:6][C@H:2]1[C:3]([O:5][CH3:9])=[O:4])=[O:19]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5460776HCID 5460776, compound

Product 1

HCID 66756837HCID 66756837, compound

Procedure

To a stirred solution of methyl (5R)-5-propynyl)-L-prolinate (1.5 g, 8.98 mmol, Example 85B) and triethylamine (1.87 mL, 13.47 mmol) in dry tetrahydrofuran (20 mL) at 0° C. was gradually added chloroacetyl chloride (0.86 mL, 10.78 mmol). 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 (DCI) m/z 244 (M+H)+.

Workup

  1. customat 0° C.
  2. filtrationthe mixture was filtered
  3. washThe solid cake was washed with THF
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-506eb7cab3684a9185f36d6d4b58cfe5
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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