Triethylamine → HCID 58887683, compound

HRID 1767214Notes

Reaction equation

HRID 1767214 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][C:5]=1[NH2:30].[C:32](Cl)(=[O:35])[CH2:33][CH3:34].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:7]=[CH:6][C:5]=1[NH:30][C:32](=[O:35])[CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 69507942HCID 69507942, compound

Product 1

HCID 58887683HCID 58887683, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[2-(2-benzyloxy-5-chlorophenyl)-cyclopent-1-enyl]-2-aminobenzoic acid methyl ester (55 mg, 0.12 mmol), propionyl chloride (13 mg, 0.14 mmol), and triethylamine (15 mg, 0.14 mmol) in dichloromethane (2 ml) was stirred at room temperature for 30 minutes. The reaction mixture was diluted with EtOAc (10 ml) and washed with 5% NaHCO3 (10 ml), 2M HCl (10 ml), water (10 ml) and brine (10 ml). The organic phase was dried and evaporated to give the product as a colourless glass 50 mg 85%. LC/MS: Rt=4.09[M+H] 490 (1 Cl).

Workup

  1. washwashed with 5% NaHCO3 (10 ml), 2M HCl (10 ml), water (10 ml) and brine (10 ml)
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-fe4b951126894b4fb299e00e4ab2cbe9
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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