Triethylamine → HCID 86609322, compound

HRID 2265768Notes

Reaction equation

HRID 2265768 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[C:1]([O:5][C:6]([N:7]([CH3:8])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)=[O:30])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68408124HCID 68408124, compound

Product 1

HCID 86609322HCID 86609322, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9a (36 mg, 0.087 mmol) was dissolved in dichloromethane (5 ml) followed by triethylamine (44 mg, 0.44 mmol). Methanesulfonyl chloride (30 mg, 0.26 mmol) was then added via a syringe. The solution was stirred at room temperature for 4 hours. After standard workup with dichloromethane, the residue was purified by silica gel preparative TLC (2.0% methanol in dichloromethane) to afford 10a (39 mg, 91%): 1H NMR δ 7.43 (d, 4H, J=8.6 Hz), 7.20 (d, 2H, J=8.4 Hz), 6.98 (q, 2H), 6.89 (d, 2H, J=8.6 Hz), 4.41 (m, 2H), 4.16 (m, 2H), 3.87 (m, 4H), 3.27 (s, 3H), 3.05 (s, 3H), 1.46 (s, 9H). Anal. (C25H33NO7S) C. H. N.

Workup

  1. customAfter standard workup with dichloromethane, the residue was purified by silica gel preparative TLC (2.0% methanol in dichloromethane)

Sources & evidence

ORD record
ord-287be14376474840bb196aa1d9cc421a
Source dataset
uspto-grants-2010_12
Patent number
US07858072B2

Reaction notes

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