Acetyl chloride → HCID 67371800, compound

HRID 1677012Notes

Reaction equation

HRID 1677012 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25]([NH:28][CH2:29][CH2:30][NH:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)(=[O:27])=[O:26].[C:40](Cl)(=[O:42])[CH3:41].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[C:40]([N:31]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)[CH2:30][CH2:29][NH:28][S:25]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[N:7]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:13])[C:6]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:26])=[O:27])(=[O:42])[CH3:41]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67372260HCID 67372260, compound

Product 1

HCID 67371800HCID 67371800, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The material from Example 96, Step C was combined with acetyl chloride (1.1 equivalents) and triethylamine (3 equivalents) in dichloromethane and stirred for for two hours at room temperature. The reaction was diluted with EtOAc, washed with sat NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to obtain the titled compound. ESI+ MS: 678 [M+H]+.

Workup

  1. washwashed
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b9b56abcc3348b2a231084dbcd88e09
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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