Ethanesulfonylchloride, 2-chloro- → HCID 58641262, compound

HRID 1394943Notes

Reaction equation

HRID 1394943 reaction equation
[Cl:1][CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH:8]1([C@H:11]([NH2:33])[C:12]([N:14]2[CH2:18][C:17]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])=[CH:16][C@H:15]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:13])[CH2:10][CH2:9]1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:1][CH2:2][CH2:3][S:4]([NH:33][C@@H:11]([CH:8]1[CH2:10][CH2:9]1)[C:12]([N:14]1[CH2:18][C:17]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:16][C@H:15]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:13])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-2×HCID 81531Diisopropylethylamine2×HCID 6102824HCID 6102824, compound

Product 1

HCID 58641262HCID 58641262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

2-chloroethanesulfonyl chloride (81 μL, 0.78 mmol, 1.1 equiv) was added to a solution of (1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethanamine (16-7, 250 mg, 0.705 mmol, 1 equiv) and N,N-diisopropylethylamine (160 μL, 0.917 mmol, 1.30 equiv) in dichloromethane (5 mL) at 0° C., and the resulting mixture was stirred for 15 minutes, then warmed to 23° C. and stirred for an additional 15 minutes. Additional 2-chloroethanesulfonyl chloride (1.2 equiv) and N,N-diisopropylethylamine (1.3 equiv) were added and the mixture was stirred for 30 minutes, then partitioned between water (75 mL) and dichloromethane (2×60 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 2-chloro-N-{(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}ethanesulfonamide (27-1) as a colorless oil. LRMS m/z (M+H—Cl) 445.4 found, 445.1 required.

Workup

  1. stirringstirred for an additional 15 minutes
  2. stirringthe mixture was stirred for 30 minutes
  3. custompartitioned between water (75 mL) and dichloromethane (2×60 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13e085c455a3494cb72bb76aa2c35cbc
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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