Diisopropylethylamine → HCID 58641354, compound

HRID 1394942Notes

Reaction equation

HRID 1394942 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH:14]1([C@H:17]([NH2:39])[C:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:19])[CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>ClCCl>[CH:14]1([C@H:17]([NH:39][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[C:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:19])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformate2×HCID 6102824HCID 6102824, compound

Product 1

HCID 58641354HCID 58641354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

4-nitrophenyl chloroformate (171 mg, 0.85 mmol, 1.5 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, 200 mg, 0.564 mmol, 1 equiv) and N,N-diisopropylethylamine (172 μL, 0.988 mmol, 1.75 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 30 minutes. Additional 4-nitrophenyl chloroformate (1.0 equiv) and N,N-diisopropylethylamine (1.0 equiv) were added and the mixture was stirred for 2.5 hours, then partitioned between water (55 mL) and dichloromethane (2×45 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present) to provide 4-nitrophenyl(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethylcarbamate (26-1) as a light yellow oil. LRMS m/z (M+H) 520.4 found, 520.2 required.

Workup

  1. stirringstirred for an additional 30 minutes
  2. stirringthe mixture was stirred for 2.5 hours
  3. custompartitioned between water (55 mL) and dichloromethane (2×45 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-b5fab83f91f644b2b8a33e04b499b193
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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