Dimethyl Sulfoxide → HCID 54503003, compound

HRID 987060Notes

Reaction equation

HRID 987060 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.C([Si](C)(C)[O:16][CH:17]([CH2:42][C:43](=[O:54])[NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1)[CH2:18][CH:19]([OH:41])[CH2:20][CH2:21][CH:22]1[CH:31]2[C:26](=[CH:27][CH:28]([CH3:39])[CH2:29][CH:30]2[O:32][C:33](=[O:38])[CH:34]([CH3:37])[CH2:35][CH3:36])[CH:25]=[CH:24][CH:23]1[CH3:40])(C)(C)C.CCN(CC)CC>C(Cl)Cl>[OH:16][CH:17]([CH2:42][C:43](=[O:54])[NH:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1)[CH2:18][C:19](=[O:41])[CH2:20][CH2:21][CH:22]1[CH:31]2[C:26](=[CH:27][CH:28]([CH3:39])[CH2:29][CH:30]2[O:32][C:33](=[O:38])[CH:34]([CH3:37])[CH2:35][CH3:36])[CH:25]=[CH:24][CH:23]1[CH3:40]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 54290098HCID 54290098, compound

Product 1

HCID 54503003HCID 54503003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.18 ml oxalyl chloride in 10 ml CH2Cl2 is slowly treated at −60° C. with 0.33 ml DMSO. After 15 minutes stirring at −60° C. a cold solution (−78° C.) of 2-methyl-butyric acid 8-[5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-(4-methoxy-benzylcarbamoyl)-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml CH2Cl2 is added. After 2 hours at −60° C., 0.80 ml of NEt3 is added and the temperature is slowly rised to room temperature. After 2 hours at room temperature the reaction is quenched with H2O. The phases are separated and the organic phase dried and concentrated. The crude product is purified by silica gel chromatography (CH2Cl2/MeOH). The resulting compound is dissolved in THF and treated with AcOH and Bu4NF.3H2O. After 30 hours the reaction mixture is concentrated, diluted with AcOEt and washed with H2O, sat. NaHCO3, brine, then dried (Na2SO4) and concentrated. The crude product is purified by silica gel chromatography. Pure fractions are combined and evaporated to afford 2-methyl-butyric acid 8-[5-hydroxy-6-(4-methoxy-benzylcarbamoyl)-3-oxo-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester as foam.

Workup

  1. additionis added
  2. customis slowly rised to room temperature
  3. customAfter 2 hours at room temperature the reaction is quenched with H2O
  4. customThe phases are separated
  5. customthe organic phase dried
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel chromatography (CH2Cl2/MeOH)
  8. dissolutionThe resulting compound is dissolved in THF
  9. additiontreated with AcOH and Bu4NF.3H2O
  10. concentrationAfter 30 hours the reaction mixture is concentrated
  11. additiondiluted with AcOEt
  12. washwashed with H2O, sat. NaHCO3, brine
  13. dry with materialdried (Na2SO4)
  14. concentrationconcentrated
  15. customThe crude product is purified by silica gel chromatography
  16. customevaporated

Sources & evidence

ORD record
ord-687d85142f1c4675971819c971bb7250
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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