Triethylamine → ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butydimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl methanesulfonate

HRID 245594Notes

Reaction equation

HRID 245594 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[CH2:12][C@@H:13]1[C@@H:17](/[CH:18]=[CH:19]/[C@@H:20]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:16]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:15][C@@H:14]1[CH2:42][OH:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:54][S:55](Cl)(=[O:57])=[O:56].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:54][S:55]([O:43][CH2:42][C@H:14]1[CH2:15][C@@H:16]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@H:17](/[CH:18]=[CH:19]/[C@@H:20]([O:26][Si:27]([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:28])[CH3:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:13]1[CH2:12][C:11]1[CH:44]=[CH:45][CH:46]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)(=[O:57])=[O:56]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86677380((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(ter-butyldimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methanol

Product 1

HCID 86677383((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butydimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl methanesulfonateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethysilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methanol (50 g, 0.075 mol) in dry CH2Cl2 (500 ml) was cooled to 0° C. under nitrogen and treated with triethylamine (31.3 ml, 0.225 mol), then with methanesulfonyl chloride (11.6 ml, 0.15 mol). The mixture was poured to saturated sodium bicarbonate aqueous and stirred for 30 minutes. The reaction mixture was phase separated and the aqueous layer was extracted with 500 ml ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 81%.

Workup

  1. customseparated
  2. extractionthe aqueous layer was extracted with 500 ml ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solid was filtered off
  5. customThe solvent was evaporated off under vacuum
  6. customThe crude product was purified by chromatography on silica gel using
  7. additiona mixture of hexane and ethyl acetate as a gradient eluent

Sources & evidence

ORD record
ord-c2f0ac15cf0a42e38c94c75f9f2345b1
Source dataset
uspto-grants-2014_02
Patent number
US08658837B2

Reaction notes

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