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Triethylamine → HCID 57655937, compound

HRID 911464
Notes
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Reaction equation

HRID 911464 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(N(CC)CC)C>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][O:29][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:26][CH:27]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57655963HCID 57655963, compound

Product 1

HCID 57655937HCID 57655937, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344Dichloromethane
Solvent

Procedure

To a stirred solution of 3-tert-butoxycarbonyl-7-chloro-6-(4-hydroxymethyl-benzylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (170 mg, 0.391 mmol) in anhydrous DCM under nitrogen, add methanesulfonyl chloride (33 μL, 0.426 mmol) and triethylamine (61 μL, 0.44 mmol) and continue stirring for 2 h. Dilute with water (5 mL) and extract three times with DCM. Wash the combined organic extracts with brine, dry over anhydrous Na2SO4, and concentrate in vacuo to obtain the desired intermediate that was used without purification.

Workup

  1. extractionextract three times with DCM
  2. washWash the combined organic extracts with brine
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-57db23bfd6f84ee6a374121fa035ceb3
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022062B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes