2,6-Dichlorobenzoyl chloride → HCID 12042590, compound

HRID 2230188Notes

Reaction equation

HRID 2230188 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:7].C(N(C(C)C)CC)(C)C.[Cl:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]([Cl:47])[C:39]=1[C:40](Cl)=[O:41]>ClCCl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:40]([C:39]2[C:38]([Cl:37])=[CH:46][CH:45]=[CH:44][C:43]=2[Cl:47])=[O:41])=[CH:24][CH:25]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[S:7]

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 12042589HCID 12042589, compound

Product 1

HCID 12042590HCID 12042590, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-N-[[1-[2-(acetylamino)ethyl]cyclopentyl]thioxomethyl]-L-phenylalanine methyl ester (195 mg, 0.498 mmol) and diisopropylethylamine (0.0950 mL, 0.548 mmol) in dichloromethane (1 mL) was added a solution of 2,6-dichlorobenzoyl chloride (110 mg, 0.523 mmol) in dichloromethane (1 mL). The resultant mixture was stirred overnight then was concentrated in vacuo and transferred to a separatory funnel containing ethyl acetate (50 mL) and water (10 mL). The separated aqueous layer back-extracted with ethyl acetate (1×25 mL). The combined organic layer was washed in turn sat. solution of Na2CO3 and brine, then was dried over MgSO4, filtered and concentrated in vacuo to provide crude N-[[1-[2-(acetylamino) ethyl]cyclopentyl]thioxomethyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester (300 mg).

Workup

  1. concentrationthen was concentrated in vacuo
  2. customtransferred to a separatory funnel
  3. additioncontaining ethyl acetate (50 mL) and water (10 mL)
  4. extractionThe separated aqueous layer back-extracted with ethyl acetate (1×25 mL)
  5. washThe combined organic layer was washed in turn sat. solution of Na2CO3 and brine
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38905b3da63d4fada8be7a939b758d6a
Source dataset
uspto-grants-2002_07
Patent number
US06423728B1

Reaction notes

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