4-Fluorobenzoyl chloride → HCID 59751437, compound

HRID 748875Notes

Reaction equation

HRID 748875 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([O:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:25][CH:24]=3)=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([OH:21])[CH:15]=[CH:14]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([O:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:25][CH:24]=3)=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([O:21][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([F:38])=[CH:40][CH:41]=2)[CH:15]=[CH:14]3)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 5327043648904-56-7

Product 1

HCID 59751437HCID 59751437, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the compound of Example 3 (111 mg, 0.21 mmol) in dichloromethane (2 mL). Add 4-fluorobenzoyl chloride (30 μL, 0.25 mmol) dropwise. After stirring for 10 minutes, pour the reaction-mixture into saturated aqueous sodium bicarbonate (10 mL) and extract with dichloromethane (10 mL). Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with methanol in dichloromethane (0 to 3%) to give 99 mg of the title compound (73%): mass spectrum (ion spray): m/z=640.3 (M+H).

Workup

  1. extractionextract with dichloromethane (10 mL)
  2. dry with materialDry the organic layer with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. washChromatograph the residue on a SiO2 column eluting with methanol in dichloromethane (0 to 3%)

Sources & evidence

ORD record
ord-68e0b900e9a94fc3ae7165ea874316ca
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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