Benzenesulfonyl chloride → HCID 58497740, compound

HRID 1616681Notes

Reaction equation

HRID 1616681 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-84cef0569bd74c74b25667875709e583
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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