Hydrochloric Acid → HCID 24755563, compound

HRID 1645434Notes

Reaction equation

HRID 1645434 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([O:12][C:13]([C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:18])=[O:17])=[O:14])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[C:22]1([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+].Cl>C(#N)C.O>[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([O:12][C:13]([C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:17])=[O:18])=[O:14])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[C:35]1([S+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21111909HCID 21111909, compound

Product 1

HCID 24755563HCID 24755563, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4.69 Parts of triphenylsulfonium 4-oxo-1-adamantyloxycarbonyldifluoromethanesulfonate was dissolved in 15 parts of acetonitrile. Into the solution was added dropwise a solution obtained by dissolving 0.15 part of sodium borohydride in 1.51 parts of ion-exchanged water. After the added mixture was stirred for 5 hours, 1N hydrochloric acid was added thereto, and extracted with 1.13 parts of chloroform. After repeatedly washed with ion exchanged water, the organic layer obtained was concentrated. To the concentrate, acetonitrile was added, then the added mixture was concentrated. The concentrate was added dropwise into ethyl acetate. The mixture was filtrated to obtain solid. The solid was dried to obtain 2.20 parts of triphenylsulfonium 4-hydroxy-1-adamantyloxycarbonyldifluoromethanesulfonate in the form of white solid, which is called as acid generator B2. As a result of analyses by 1H-NMR and LCMS, the acid generator B2 determined to be a mixture of two isomers.

Workup

  1. additionInto the solution was added dropwise a solution
  2. customobtained
  3. extractionextracted with 1.13 parts of chloroform
  4. washAfter repeatedly washed with ion
  5. customthe organic layer obtained
  6. concentrationwas concentrated
  7. additionTo the concentrate, acetonitrile was added
  8. concentrationthe added mixture was concentrated
  9. additionThe concentrate was added dropwise into ethyl acetate
  10. filtrationThe mixture was filtrated
  11. customto obtain solid
  12. customThe solid was dried

Sources & evidence

ORD record
ord-768717699c4d45b295258e413c343d8a
Source dataset
uspto-grants-2012_02
Patent number
US08124803B2

Reaction notes

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