Triethylamine → 2-(2-Benzoyloxypropan-1-yl)-3-hexadecylthiopropanol methanesulfonate

HRID 728507Notes

Reaction equation

HRID 728507 reaction equation
[C:1]([O:9][CH:10]([CH3:33])[CH2:11][CH:12]([CH2:15][S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:13][OH:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C.N(CC(NC(OC)=O)CSCCCCCCCCCCCCCCCC)=[N+]=[N-]>ClCCl>[CH3:34][S:35]([O:14][CH2:13][CH:12]([CH2:11][CH:10]([O:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:33])[CH2:15][S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 148349922-(2-Benzoyloxypropan-1-yl)-3-hexadecylthiopropanolHCID 148350943-Azido-1-hexadecylthio-2-methoxycarbonylaminopropane

Product 1

HCID 536352672-(2-Benzoyloxypropan-1-yl)-3-hexadecylthiopropanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.268 g (2.65 mM) of 2-(2-benzoyloxypropan-1-yl)-3-n-hexadecylthiopropanol m12, 0.270 ml (3.45 mM) of methanesulfonyl chloride and 0.56 ml (3.98 mM) of triethylamine in 30 ml of dichloromethane is allowed to react by the same procedure as described in (52) and the crude product of the titled compound m12a is obtained.

Workup

  1. customto react by the same procedure

Sources & evidence

ORD record
ord-38b9091d7344456e8154a5a4554ff15b
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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