Diisopropylethylamine → HCID 71656887, compound

HRID 2278173Notes

Reaction equation

HRID 2278173 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15](=[O:22])[CH:16]([C:18]([F:21])([F:20])[F:19])[OH:17].C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1>C(Cl)Cl>[Cl:52][C:49]1[CH:50]=[CH:51][C:46]([CH:39]([C:36]2[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][CH:37]=2)[N:40]2[CH2:41][CH2:42][N:43]([C:2]([O:17][CH:16]([C:15]([O:14][CH3:13])=[O:22])[C:18]([F:21])([F:20])[F:19])=[O:4])[CH2:44][CH2:45]2)=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 2855101-[Bis(4-chlorophenyl)methyl]piperazineHCID 2760118methyl 3,3,3-trifluoro-dl-lactate

Product 1

HCID 71656887HCID 71656887, compoundYield 140.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of triphosgene (65 mg, 0.22 mmol) in CH2Cl2 (5.0 mL) was added methyl-3,3,3-trifluoro-DL-lactate (116 mg, 0.73 mmol) followed by N,N-diisopropylethylamine (0.38 mL, 2.19 mmol). After 2 h, 1-(bis(4-chlorophenyl)methyl)piperazine (160 mg, 0.50 mmol) was added as a solution in CH2Cl2 (2 mL) and stirred for another 2 h. The mixture was concentrated under reduced pressure and purified directly by SiO2 flash chromatography (25% EtOAc/hexanes) to provide the titled compound (156 mg, 62%): 1H NMR 500 MHz (CDCl3) δ 7.31 (d, J=8.47 Hz, 4H), 7.26 (d, J=8.41 Hz, 4H), 5.43 (q, J=7.03 Hz, 1H), 4.23 (s, 1H), 3.85 (s, 3H), 3.66-3.46 (m, 4H), 2.44-2.32 (m, 4H); HRMS m/z calc'd for [M+H]+ C22H21Cl2F3N2O4: 505.0903. found 505.0905.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified directly by SiO2 flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a03a136ef2294680b63bf96528f9c3b7
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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