Triethylamine → HCID 66590255, compound

HRID 2363522Notes

Reaction equation

HRID 2363522 reaction equation
[CH2:1]1[C@@H:5]2[CH2:6][CH2:7][C@@H:8]([NH:9][C:10](=[O:25])[C@H:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:13])[C@@H:4]2[CH2:3][NH:2]1.C(N(CC)CC)C.[F:33][C:34]([F:46])([F:45])[C:35]1[CH:36]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1>ClCCl>[C:17]([O:16][C:14]([N:12]([CH3:13])[C@H:11]([C:10]([NH:9][C@H:8]1[C@H:4]2[C@H:5]([CH2:1][N:2]([S:41]([C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([C:34]([F:33])([F:45])[F:46])[CH:36]=3)(=[O:43])=[O:42])[CH2:3]2)[CH2:6][CH2:7]1)=[O:25])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:15])([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66589977HCID 66589977, compound

Product 1

HCID 66590255HCID 66590255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N1-[(3aS,4R,6aR)-Octahydrocyclopenta[c]pyrrol-4-yl]-N2-(tert-butyloxycarbonyl)-N2-methyl-L-leucinamide from Step A (220 mg, 0.622 mmol) in dichloromethane (5.0 mL) was added triethylamine (0.130 mL, 0.934 mmol) followed by 3-(trifluoromethyl)benzene-1-sulfonyl chloride (0.110 mL, 0.685 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction was reduced in volume and loaded onto a silica gel cartridge (Analogix®, Burlington, Wis., RS-24). The title compound was eluted with a gradient of 0% to 10% methanol (2 N ammonia)/dichloromethane over 20 minutes to give N2-(tert-butyloxycarbonyl)-N2-methyl-N1-((3aS,4R,6aR)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.32 (bs, 1H), 8.18-8.13 (m, 1H), 8.02-7.95 (m, 1H), 7.90-7.84 (m, 1H), 7.68 (t, J=7.9, 1H), 4.17-4.09 (m, 1H), 3.77-3.69 (m, 1H), 3.20-3.11 (m, 2H), 3.05-2.97 (m, 4H), 2.53-2.47 (m, 2H), 1.98-1.88 (m, 1H), 1.87-1.71 (m, 3H), 1.62-1.48 (m, 3H), 1.46 (s, 9H), 1.32-1.22 (m, 1H), 0.87 (dd, J=6.6, 15.5, 6H).

Workup

  1. washThe title compound was eluted with a gradient of 0% to 10% methanol (2 N ammonia)/dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-efa0de23ef1a473cbddb61df16171f52
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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