Hydrochloric Acid → HCID 22467291, compound

HRID 1934560Notes

Reaction equation

HRID 1934560 reaction equation
[C:1]1([N:7]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:8](=[O:42])[O:9][CH2:10][C:11]2([OH:41])[CH2:17][CH2:16][CH2:15][C:14]3[C:18]([O:22][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]2[OH:40])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N(C2C=CC=CC=2)C(=O)OCC2(O)C(O)CCC3C(O[Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3C2)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[C:43]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:42])[O:9][CH2:10][C:11]2([OH:41])[CH2:17][CH2:16][CH2:15][C:14]3[C:18]([OH:22])=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]2[OH:40])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 22467311HCID 22467311, compoundHCID 22467321HCID 22467321, compound

Product 1

HCID 22467291HCID 22467291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a mixture of [(5SR,6SR)-1-(tert-butyldiphenylsilyloxy)-5,6-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate and [(6RS,7RS)-1-(tert-butyldiphenylsilyloxy)-6,7-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (1.04 g) in THF (10 ml) was added tetrabutylammonium fluoride (1M THF solution, 2.38 ml) at 5° C. The mixture was stirred at room temperature for 1 hour. After addition of 1N-hydrochloric acid (3 ml) under ice-cooling, the mixture was extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogencarbonate solution, water, and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 4:5) to give first [(5SR,6SR)-1,5,6-trihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (468.4 mg) as an amorphous solid and then [(6RS,7RS)-1,6,7-trihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (195.9 mg) as an amorphous solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with water, saturated sodium hydrogencarbonate solution, water
  4. dry with materialIt was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 4:5)

Sources & evidence

ORD record
ord-5eecad7e20704cc79b9fdfc4c9fce2b2
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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