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Benzenesulfonyl chloride, 3,4-dichloro- → tert-Butyl trans-6-[(3,4-dichlorophenyl)sulfonyl]-6,7,7a,8,10,10a-hexahydropyrido[3,2-c]pyrrolo[3,4-e]azepine-9(5H)-carboxylate

HRID 84967
Notes
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Reaction equation

HRID 84967 reaction equation
[N:1]1[C:11]2[C@@H:10]3[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C@H:9]3[CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:29][C:30]1[CH:31]=[C:32]([S:37](Cl)(=[O:39])=[O:38])[CH:33]=[CH:34][C:35]=1[Cl:36].[OH-].[Na+]>ClCCl>[Cl:29][C:30]1[CH:31]=[C:32]([S:37]([N:7]2[CH2:8][C@@H:9]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][C@H:10]3[C:11]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:6]2)(=[O:38])=[O:39])[CH:33]=[CH:34][C:35]=1[Cl:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 123947677tert-Butyl trans-6,7,7a,8,10,10a-hexahydropyrido[3,2-c]pyrrolo[3,4-e]azepine-9(5H)-carboxylate

Product 1

HCID 123445055tert-Butyl trans-6-[(3,4-dichlorophenyl)sulfonyl]-6,7,7a,8,10,10a-hexahydropyrido[3,2-c]pyrrolo[3,4-e]azepine-9(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 334B (100 mg, 0.34 mmol) and triethylamine (0.097 mL, 0.69 mmol) in dichloromethane (2 mL) was stirred at ambient temperature for 10 minutes. 3,4-Dichlorobenzene-1-sulfonyl chloride (0.52 mmol, 1.5 equivalents) was added, and the reaction mixture was stirred at room temperature overnight. A 10% NaOH solution (2 mL) was added; the dichloromethane layer was separated, treated with water (2 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the title compound.

Workup

  1. customthe dichloromethane layer was separated
  2. additiontreated with water (2 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f6e17a941eae4d229020d7b4426a778f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846951B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes