Triethylamine → HCID 68767961, compound

HRID 1374354Notes

Reaction equation

HRID 1374354 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([N:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:14])[CH2:9][C@H:8]2[C:19]([O:21][CH3:22])=[O:20])[C:3]1=[O:23].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](O)=[O:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[C:15]([N:13]([CH3:14])[C@H:10]1[CH2:9][C@@H:8]([C:19]([O:21][CH3:22])=[O:20])[C@@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=3)[C:3]2=[O:23])[CH2:12][CH2:11]1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 99633-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68768096HCID 68768096, compound

Product 1

HCID 68767961HCID 68767961, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,2S,5R)-methyl 2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(tert-butyl(methyl)amino)-cyclohexanecarboxylate (58 mg, 0.18 mmol), 3-(trifluoromethyl)benzoic acid (42 mg, 0.22 mol), EDCI (30 mg, 0.21 mmol), HOBT (30 mg, 0.21 mmol), and Et3N (21 mg 0.21 mmol) in CH2Cl2 was stirred overnight at room temperature. The solution was washed with water and brine, concentrated in vacuo and the residue chromatographed on silica gel (3%–5%–10% (NH4OH/MeOH)/CH2Cl2) to give 34 mg of the title product, (1R,2S,5R)-methyl 5-(tert-butyl(methyl)amino)-2-((S)-2-oxo-3-(3-(trifluoromethyl)-benzamido)pyrrolidin-1-yl)cyclohexanecarboxylate, as a white solid. MS found: (M+H)+=498.40.

Workup

  1. washThe solution was washed with water and brine
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed on silica gel (3%–5%–10% (NH4OH/MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-7c1fa98505c84fc68961dfb5f5938b3a
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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