Chloroacetyl chloride → HCID 69781315, compound

HRID 1061540Notes

Reaction equation

HRID 1061540 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]([CH:10]1[CH2:19][CH:18]2[CH:13]([CH:14]=[C:15]([O:22][CH3:23])[C:16]([O:20][CH3:21])=[CH:17]2)[CH:12]([C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[NH:11]1)=[O:9].CCN(CC)CC>C(Cl)Cl>[CH3:6][O:7][C:8]([CH:10]1[CH2:19][CH:18]2[CH:13]([CH:14]=[C:15]([O:22][CH3:23])[C:16]([O:20][CH3:21])=[CH:17]2)[CH:12]([C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[N:11]1[C:3](=[O:4])[CH2:2][Cl:1])=[O:9]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 69780933HCID 69780933, compound

Product 1

HCID 69781315HCID 69781315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (0.23 mL), 2.88 mmol) was added dropwise to a mixture of Intermediate 7 (0.82 g, 2.21 mmol) and Et3N (0.71 mL, 5.09 mmol) in CH2Cl2 (15 mL) at 0° C. under a nitrogen blanket. The resulting mixture was warmed to room temperature and stirred for about 0.5 hour. The reaction was quenched with 1 N HCl (2 mL), and diluted with CH2Cl2 (50 mL) and-water (10 mL). The layers were separated and the organic was washed with saturated NaCl and dried over anhydrous Na2SO4. Filtration and concentration in vacuo afforded Intermediate 8 (1.5 g), which was used without further purification. TLC Rf (10% EtOAc/CH2Cl2)=0.55; MS (API) m/z 448 (M+H), 472 (M+Na).

Workup

  1. customThe reaction was quenched with 1 N HCl (2 mL)
  2. additiondiluted with CH2Cl2 (50 mL)
  3. customThe layers were separated
  4. washthe organic was washed with saturated NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-36b0f08d99d74f81bba4745c7b112be5
Source dataset
uspto-grants-2005_11
Patent number
US06960587B2

Reaction notes

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