Cyclopentanecarbonyl chloride → ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetate

HRID 1790580Notes

Reaction equation

HRID 1790580 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:18]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=1.C(N(C(C)C)CC)(C)C.OS([O-])(=O)=O.[K+]>C(Cl)Cl>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([NH:24][CH:18]([C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[CH:15]=[C:10]([NH:9][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:11]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:26][CH:27]=1)#[N:32]

Participants

6

Reactant 4

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 86583558ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate

Product 1

HCID 86583560ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetateYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentanecarbonyl chloride (0.104 ml, 0.85 mmol) was added dropwise at 0° C. to a solution of the ethyl (RS)-(3-amino-5-ethyl-phenyl)-(4-cyano-phenylamino)-acetate (250 mg, 0.772 mmol) obtained in Example 223.4 and diisopropylethylamine (0.146 ml, 0.85 mmol) in CH2Cl2 (5 ml). The reaction mixture was warmed slowly (2 h.) to room temperature. A saturated aqueous solution of KHSO4 was added and the mixture was extracted with EtOAc. The organic phase was washed with H2O, dried and filtered, and the filtrate was concentrated. The residue was purified by chromatography (SiO2, hexane->hexane/EtOAc 2:1). There were obtained 215 mg (66%) of ethyl (RS)-(4-cyano-phenylamino)-[3-(cyclopentanecarbonyl-amino)-5-ethyl-phenyl]-acetate as a colorless foam; MS: 418 ([M−H]−).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (SiO2, hexane->hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-c10e5641a76c48b9955287bda5602d73
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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