Triethylamine → HCID 57655937, compound

HRID 2041343Notes

Reaction equation

HRID 2041343 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]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57655963HCID 57655963, compound

Product 1

HCID 57655937HCID 57655937, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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-62591cd26a8944709a0ee20bac170cf7
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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