Triethylamine → 13-Oxo-17,17,17-triphenyl-3,6,9-trioxa-16-thia-12-azaheptadec-1-yl methanesulfonate

HRID 1845721Notes

Reaction equation

HRID 1845721 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:42])[CH2:20][CH2:21][S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:42])[CH2:20][CH2:21][S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68927996N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide

Product 1

HCID 8662693113-Oxo-17,17,17-triphenyl-3,6,9-trioxa-16-thia-12-azaheptadec-1-yl methanesulfonateYield 121.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.55 mL, 7.1 mmol) was added to a 0° C. solution of N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide (3.38 g, 6.45 mmol) and triethylamine (1.08 mL, 7.74 mmol) in dichloromethane (33 mL). The solution was allowed to warm to room temperature. After 4 hours, the solution was diluted with dichloromethane and washed with water (2×) and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 4.71 g of 13-oxo-17,17,17-triphenyl-3,6,9-trioxa-16-thia-12-azaheptadec-1-yl methanesulfonate, which was concentrated from toluene and used in Part C.

Workup

  1. washwashed with water (2×) and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fc1b47f215f4d87b1646672fea9870f
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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