Benzoyl chloride → HCID 66590127, compound

HRID 2363541Notes

Reaction equation

HRID 2363541 reaction equation
[CH3:1][CH:2]([CH3:21])[CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]([NH:6][C@@H:7]1[C@@H:14]2[C@@H:10]([CH2:11][NH:12][CH2:13]2)[CH2:9][CH2:8]1)=[O:5].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:29]([N:12]1[CH2:13][C@@H:14]2[C@@H:7]([NH:6][C:4](=[O:5])[CH:3]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:2]([CH3:21])[CH3:1])[CH2:8][CH2:9][C@@H:10]2[CH2:11]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 665906853-Methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide

Product 1

HCID 66590127HCID 66590127, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide from Example 83 Step A (25 mg, 0.087 mmol), triethylamine (0.018 mL, 0.131 mmol), and benzoyl chloride (10.12 μL, 0.087 mmol) were combined in dichloromethane (5 mL). After 5 minutes, TLC shows no more starting material. The crude reaction mixture was concentrated and applied to a silica gel cartridge (Analogix®, Burlington, Wis., RS-4) eluting with 1-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.49-7.42 (m, 2H), 7.41-7.35 (m, 3H), 7.33-7.27 (m, 3H), 5.43 (d, J=6.7, 1H), 3.97 (m, 1H), 3.74 (m, 2H), 3.56 (m, 2H), 3.39 (m, 1H), 2.74 (m, 2H), 2.48 (m, 1H), 2.38 (m, 2H), 2.07 (dd, J=4.6, 10.8, 1H), 1.94 (m, 1H), 1.52-1.31 (m, 2H), 1.01 (d, J=6.3, 3H), 0.68 (d, J=6.6, 3H); MS (ESI+) m/z 391 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. washeluting with 1-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-073df8f270cb453a9a6698516ab60d0c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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