Benzenesulfonyl chloride → HCID 58497740, compound

HRID 1519218Notes

Reaction equation

HRID 1519218 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C@@H:12]1[CH2:16][CH2:15][C@@H:14]([C:17]([N:19]2[CH2:26][CH2:25][C@:24]3([CH3:30])[C:27]([CH3:29])([CH3:28])[C@H:20]2[CH2:21][C:22]2[C:34]([OH:35])=[CH:33][CH:32]=[CH:31][C:23]=23)=[O:18])[CH2:13]1.C(N(CC)CC)C>ClCCl>[OH:35][C:34]1[C:22]2[CH2:21][C@@H:20]3[C:27]([CH3:29])([CH3:28])[C@:24]([CH3:30])([C:23]=2[CH:31]=[CH:32][CH:33]=1)[CH2:25][CH2:26][N:19]3[C:17]([C@@H:14]1[CH2:15][CH2:16][C@@H:12]([NH:11][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH2:13]1)=[O:18]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 58497679HCID 58497679, compound

Product 1

HCID 58497740HCID 58497740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (41 mg) is added to a solution of [(1R,3R)-3-amino-cyclopentyl]-[(2R,6S)-10-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-methanone (80 mg) and triethylamine (120 μL) in dichloromethane (1 mL). The resulting solution is stirred at room temperature overnight and then concentrated under reduced pressure. The residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H) to give the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H)

Sources & evidence

ORD record
ord-7bfa4716f0ec4c6ebaefe07305fa21fd
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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