Water → HCID 53645409, compound

HRID 326928Notes

Reaction equation

HRID 326928 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@H:20](OS(C)(=O)=O)[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C@@H:29]([CH2:39][CH3:40])[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:52][C:53]([CH3:59])([CH3:58])[CH2:54][CH2:55][CH2:56][SH:57].O>CC#N>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([S:57][CH2:56][CH2:55][CH2:54][C:53]([OH:52])([CH3:59])[CH3:58])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C@@H:29]([CH2:39][CH3:40])[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 540229832-Methyl-5-sulfanylpentan-2-olHCID 54164197HCID 54164197, compound

Product 1

HCID 53645409HCID 53645409, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of mesylate of Step 6 (4.4 g, 66 mmol) and Cs2CO3 (4.3 g, 132 mmol) in CH3CN (44 mL) was degassed and then purged with N2. The suspension was then cooled to 0° C. and 4-hydroxy-4-methyl-1-pentanethiol (Step 7, 1.8 mL, 132 mmol) was added. The reaction was stirred for 30 min at 0° C. followed by 3 h at r.t. Water (50 mL) was then added and the product was extracted with EtOAc. The organic layer was washed with H2O and saturated NaCl solution. The solvent was removed under vacuum and the crude product was purified by flash chromatography (1:20 and 1:10 EtOAc:toluene) to give the title compound as an off-white foam (4.25 g).

Workup

  1. customwas degassed
  2. custompurged with N2
  3. waitfollowed by 3 h at r.t
  4. extractionthe product was extracted with EtOAc
  5. washThe organic layer was washed with H2O and saturated NaCl solution
  6. customThe solvent was removed under vacuum
  7. customthe crude product was purified by flash chromatography (1:20 and 1:10 EtOAc:toluene)

Sources & evidence

ORD record
ord-0c8eee56256140e198ec882612871a50
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

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