Sodium Carbonate → 3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[(1S)-2-hydroxy-1-phenylethyl]benzenesulfonamide

HRID 421775Notes

Reaction equation

HRID 421775 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH2:14]1[NH:19][CH2:18][CH2:17][N:16]2[CH2:20][CH2:21][CH2:22][C@H:15]12.C(=O)([O-])[O-].[Na+].[Na+].[NH2:29][C@@H:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:31][OH:32]>ClCCl.CN(C)C=O.CO>[CH2:14]1[N:19]([C:8]([C:7]2[CH:6]=[C:5]([S:2]([NH:29][C@@H:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:31][OH:32])(=[O:4])=[O:3])[CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:18][CH2:17][N:16]2[CH2:20][CH2:21][CH2:22][C@H:15]12

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 1347972-Amino-2-phenylethan-1-olHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazine

Product 1

HCID 468524393-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[(1S)-2-hydroxy-1-phenylethyl]benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 3-(chlorosulfonyl)benzoyl chloride (0.359 g, 1.5 mmol) in anhydrous dichloromethane (40 mL) was added (R)-octahydropyrrolo[1,2-a]pyrazine (0.189 g, 1.5 mmol) in dichloromethane (4 mL) slowly over 10 min at room temperature. Then sodium carbonate (0.48 g, 4.52 mmol) was added. The mixture was stirred at room temperature overnight. Then (S)-2-amino-2-phenylethanol (0.274 g, 2.0 mmol) in N,N-dimethylformamide (10 mL) was added. The mixture was stirred at room temperature for 4 days. Then methanol (5 mL) was added, the mixture was stirred for 20 minutes, then filtered, and concentrated. The residue was purified by chromatography on silica gel (methanol/dichloromethane=1:12) to give the titled compound: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.30 (m, 1H), 1.60-2.10 (m, 6H), 2.80-3.10 (m, 4H), 3.40 (m, 3H), 4.25 (m, 1H), 4.40-4.60 (m, 1H), 4.82 (t, 1H, J=4 Hz), 7.10 (m, 5H), 7.44 (m, 2H), 7.60 (s, 1H), 7.65 (m, 1H), 8.30 (d, 1H, J=7 Hz); MS (ESI) m/z 430 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 days
  2. stirringthe mixture was stirred for 20 minutes
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (methanol/dichloromethane=1:12)

Sources & evidence

ORD record
ord-71df9ee5e923440d8bdd1b476a04741c
Source dataset
uspto-grants-2012_01
Patent number
US08101614B2

Reaction notes

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