Chloroacetyl chloride → HCID 23449825, compound

HRID 1838804Notes

Reaction equation

HRID 1838804 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Cl:34][CH2:35][C:36](Cl)=[O:37]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[C:36](=[O:37])[CH2:35][Cl:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 131724289HCID 131724289, compound

Product 1

HCID 23449825HCID 23449825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Compound 11 (1.0 g, 3.0 mmol) was dissolved in 20 mL DCM and treated with diisopropylethyl amine (0.76 g, 4.5 mmol). The mixture was cooled to ° C. To the cold mixture was added dropwise chloroacetyl chloride in 5 mL DCM. The reaction mixture was allowed to stir at RT for 24 h. The mixture was diluted with 50 mL DCM and washed with 50 mL of water and 10% citric acid. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated under reduced pressure and the residue was crystallized from ethylether to afford compound 12.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with 50 mL of water and 10% citric acid
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was crystallized from ethylether

Sources & evidence

ORD record
ord-20906d445a4a48f6b0e9f3eb44194bbf
Source dataset
uspto-grants-2004_01
Patent number
US06677336B2

Reaction notes

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