Dimethyl Sulfoxide → HCID 86591972, compound

HRID 984536Notes

Reaction equation

HRID 984536 reaction equation
[OH:1][CH2:2][CH:3]([CH3:42])[CH2:4][CH2:5][CH2:6][C:7]([CH3:41])=[CH:8][CH2:9][CH:10]([O:20][C:21](=[O:40])[CH2:22][C@H:23]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:24]([CH3:31])([CH3:30])[C:25](=[O:29])[CH:26]([Br:28])[CH3:27])[C:11]([CH3:19])=[CH:12][C:13]1[N:14]=[C:15]([CH3:18])[S:16][CH:17]=1.CS(C)=O.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH3:41][C:7]([CH2:6][CH2:5][CH2:4][CH:3]([CH3:42])[CH:2]=[O:1])=[CH:8][CH2:9][CH:10]([O:20][C:21](=[O:40])[CH2:22][C@H:23]([O:32][Si:33]([C:36]([CH3:37])([CH3:38])[CH3:39])([CH3:35])[CH3:34])[C:24]([CH3:30])([CH3:31])[C:25](=[O:29])[CH:26]([Br:28])[CH3:27])[C:11]([CH3:19])=[CH:12][C:13]1[N:14]=[C:15]([CH3:18])[S:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 8471TriethylamineHCID 86591973HCID 86591973, compound

Product 1

HCID 86591972HCID 86591972, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

180 mg (0.262 mmol) (3S)-6-bromo-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-5-oxo-heptanoic acid 9-hydroxy-4,8-dimethyl-1-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-non-3-enyl ester (277b) were dissolved in 5.30 mL CH2Cl2 and 1.72 mL DMSO at 0° C. and 212 μl (155 mg, 1.53 mmol) triethylamine were added. After addition of 195 mg (1.223 mmol) SO3.Pyridine—complex the mixture was stirred 60 min at 0° C. Dilution with 40 mL diethylether was followed by twofold washing with 10 mL demi water and with brine (2×10 mL). The organic layer was the dried over Na2SO4, filtered and concentrated in vacuo to give a slightly yellow oil which was used in the following reaction step without further purification.

Workup

  1. additionAfter addition of 195 mg (1.223 mmol) SO3
  2. washby twofold washing with 10 mL demi water and with brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a slightly yellow oil which
  7. customwas used in the following reaction step without further purification

Sources & evidence

ORD record
ord-9e061a1eb4c4495d91c357c175ed62c3
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

Loading…