2,6-Dichlorobenzoyl chloride → HCID 12042611, compound

HRID 990141Notes

Reaction equation

HRID 990141 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:7].[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:32]=1[C:33](Cl)=[O:34].C(N(C(C)C)CC)(C)C>ClCCl.O>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:33]([C:32]2[C:31]([Cl:30])=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:40])=[O:34])=[CH:24][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:7]

Participants

6

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 54107824HCID 54107824, compound

Product 1

HCID 12042611HCID 12042611, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-N-[[1-[4-(methylsulfonyl)butyl]cyclopentyl]thioxomethyl]-L-phenylalanine methyl ester (19.0 mmol, 8.37 g) and 2,6-dichlorobenzoyl chloride (21 mmol, 4.4 g) in dichloromethane (90 mL) was added diisopropylethylamine (32.3 mmol, 5.6 mL) at room temperature. The solution was stirred for 15 h at which time TLC analysis of the mixture indicated the absence of starting material. Then, it was diluted with water (100 mL) and the two layers were separated. The aqueous phase was extracted with dichloromethane (100 mL) and the combined extracts were washed with brine (200 mL). The dried (MgSO4) solution was concentrated under vacuum and the residue was purified by silica gel column chromatography eluting with (hexane:ethyl acetate:dichloromethane, 1:1:1) to obtain 11.54 g (99%) of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-[4-(methylsulfonyl)butyl]cyclopentyl]thioxomethyl]-L-phenylalanine methyl ester as a colorless solid, mp 200-202° C. HRMS: Obs. mass, 613.1367. Calcd. mass, 613.1363 (M+H).

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous phase was extracted with dichloromethane (100 mL)
  3. washthe combined extracts were washed with brine (200 mL)
  4. dry with materialThe dried (MgSO4) solution
  5. concentrationwas concentrated under vacuum
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with (hexane:ethyl acetate:dichloromethane, 1:1:1)

Sources & evidence

ORD record
ord-73c4b6f179474ddfb42ab828490205b6
Source dataset
uspto-grants-2002_10
Patent number
US06458844B2

Reaction notes

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