Oxalyl chloride → HCID 86647508, compound

HRID 2194317Notes

Reaction equation

HRID 2194317 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][C:39]1[N:40]=[C:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:42][C:43]=1[CH3:44])[CH2:12][N:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([O:26][CH2:27][CH2:28][CH:29]([CH3:33])[C:30](O)=[O:31])[C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2>ClCCCl.CN(C)C=O>[CH3:44][C:43]1[O:42][C:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[N:40][C:39]=1[CH2:38][O:37][C:36]1[CH:35]=[CH:34][C:11]([CH2:12][N:13]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([O:26][CH2:27][CH2:28][CH:29]([CH3:33])[C:30]([Cl:4])=[O:31])[C:20]=3[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]=1[O:8][CH3:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 11714078HCID 11714078, compound

Product 1

HCID 86647508HCID 86647508, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

2.2 mL of oxalyl chloride was added to the solution of 10.0 g of (±)-4-{9-[3-methoxy-4-((5-methyl-2-phenyloxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}-2-methyl-butyric acid prepared by the example 27 in 1,2-dichloroethane (100 mL), and then 5 drops of N,N-dimethylformamide was added thereto, and stirred at room temperature for 1 hour. The reaction mixture was vacuum concentrated, and (±)-4-(9-(4-((5-methyl-2-phenyloxazole-4-yl)methoxy)-3-methoxybenzyl)-9H-carbazole-4-yloxy)-2-methylbutanoyl chloride was prepared.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-b4785cde2b254a3d87b11e7b890a5274
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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