Triethylamine → HCID 76485058, compound

HRID 1599669Notes

Reaction equation

BrCCCS(Cl)(=O)=O.NCC[CH2:12][CH2:13][S:14]([NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:41])[CH:25]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:16])=[O:15].[CH2:42]([N:44](CC)CC)C>ClCCl>[NH2:44][CH2:42][CH2:12][CH2:13][S:14]([NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:41])[CH:25]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:15])=[O:16]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of Part A 3-bromopropyl sulfonyl chloride (1.06 g, 4.8 mmol) in dichloromethane (5 mL) was added dropwise to a cooled (-10° C.) stirred solution of Example 6a, Part B amine (1.05 g, 3.02 mmol) and triethyl amine (1.44 mL, 9.6 mmol) in dichloromethane (15 mL), After a few minutes, a precipitate formed. The suspension was stirred at -10° C. for 2.5 hours, diluted with dichloromethane (35 mL) and washed with 1N HCl solution (2×15 mL). The dichloromethane solution was dried (MgSO4), filtered and the solvent was removed in vacuo. The crude oil was purified on silica gel (Merck, 150 mL) eluting with 50% ethyl acetate in hexane to give title compound as a white foam (1.160 g, 72%).

Workup

waitAfter a few minutes
customa precipitate formed
washwashed with 1N HCl solution (2×15 mL)
dry with materialThe dichloromethane solution was dried (MgSO4)
filtrationfiltered
customthe solvent was removed in vacuo
customThe crude oil was purified on silica gel (Merck, 150 mL)
washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-ad2514f72cba405ead6c86388790ef77
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741799

Reaction notes

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