Hydrochloric Acid → HCID 86632757, compound

HRID 1670364Notes

Reaction equation

HRID 1670364 reaction equation
[F:1][C:2]([F:9])([S:5]([O-:8])(=[O:7])=[O:6])[CH2:3][OH:4].[C:10]1([S+:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[C:36]12([C:47](Cl)=[O:48])[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([C:39]3=[O:46])[CH2:37]1)[CH2:43]2.Cl>C(#N)C.CCOCC.C(C(C)=O)C(C)C>[C:36]12([C:47]([O:4][CH2:3][C:2]([F:9])([F:1])[S:5]([O-:8])(=[O:7])=[O:6])=[O:48])[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([C:39]3=[O:46])[CH2:37]1)[CH2:43]2.[C:23]1([S+:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 573525194-Oxotricyclo[3.3.1.1~3,7~]decane-1-carbonyl chlorideHCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate

Product 1

HCID 86632757HCID 86632757, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

In 20 g of acetonitrile, 5.4 g (0.01 mole) of the intermediate, triphenylsulfonium 1,1-difluoro-2-hydroxy-ethanesulfonate (purity 78%), 1.0 g (0.01 mole) of triethylamine and 0.24 g (0.002 mole) of N,N-dimethylaminopyridine were dissolved and ice cooled. 2.6 g (0.012 mole) of 4-adamantanone-1-carbonyl chloride, prepared above, was added dropwise to the solution at a temperature below 5° C. It was stirred at room temperature for 1 hour. Dilute hydrochloric acid (1 g of 12N hydrochloric acid in 10 g of water) was added to the solution. The acetonitrile was distilled off in vacuum, after which 50 g of dichloromethane, 50 g of methyl isobutyl ketone, and 20 g of water were added to the residue. The organic layer was separated and washed with 20 g of water. The solvent was distilled off in vacuum. Ether was added to the residue for crystallization. The crystals were filtered and dried, obtaining the target compound. 4.8 g (yield 80%). On 1H-NMR analysis, methyl isobutyl ketone and ether were observed as a trace amount of residual solvent.

Workup

  1. temperatureice cooled
  2. additionwas added dropwise to the solution at a temperature below 5° C
  3. distillationThe acetonitrile was distilled off in vacuum
  4. additionafter which 50 g of dichloromethane, 50 g of methyl isobutyl ketone, and 20 g of water were added to the residue
  5. customThe organic layer was separated
  6. washwashed with 20 g of water
  7. distillationThe solvent was distilled off in vacuum
  8. additionEther was added to the residue for crystallization
  9. filtrationThe crystals were filtered
  10. customdried
  11. customobtaining the target compound

Sources & evidence

ORD record
ord-005fff04cbdb43028d55f6db138f8924
Source dataset
uspto-grants-2011_08
Patent number
US07993811B2

Reaction notes

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