Trifluoroacetic acid → HCID 59013481, compound

HRID 1716974Notes

Reaction equation

HRID 1716974 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]1([C:41]1[CH:46]=[C:45]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([CH2:54][CH3:55])=[CH:50][CH:49]=2)[C:44]([Cl:56])=[CH:43][C:42]=1[CH:57]=[CH2:58])O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=[O:60].O[Li].O>C1COCC1.CO.O>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:41]1[C:42](=[CH:43][C:44]([Cl:56])=[C:45]([CH2:47][C:48]3[CH:49]=[CH:50][C:51]([CH2:54][CH3:55])=[CH:52][CH:53]=3)[CH:46]=1)[CH:57]([OH:60])[CH2:58]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 59467876HCID 59467876, compound

Product 1

HCID 59013481HCID 59013481, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-5-(4-ethylbenzyl)-2-vinylphenyl)tetrahydro-2H-pyran-2-ol (120 mg, 0.15 mmol) was added TFA (1.5 mL) at −10° C. After the reaction mixture was stirred for 6 h, the solvent was removed under vacuum and aqueous saturated NaHCO3 (10 mL) was added to the residue. The aqueous layer was extracted with EtOAc (10 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. Removal of the solvent afforded the crude product, which was dissolved in 1.9 mL of a mixture of THF:CH3OH:H2O (2:3:1) followed by addition of 6 mg of LiOH.H2O at room temperature. After stirring for 2 h, the volatiles were removed using a rotary evaporator. The residue, after being dissolved in ethyl acetate, was washed with brine (10 mL×2), 5% aqueous KHSO4 (10 mL) and finally with brine (10 mL) prior to drying over Na2SO4. The volatiles were removed and the resulting oil was purified by preparative TLC to obtain 44 mg of the title product.

Workup

  1. customthe solvent was removed under vacuum and aqueous saturated NaHCO3 (10 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous layer was extracted with EtOAc (10 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. customafforded the crude product, which
  8. stirringAfter stirring for 2 h
  9. customthe volatiles were removed
  10. customa rotary evaporator
  11. dissolutionThe residue, after being dissolved in ethyl acetate
  12. washwas washed with brine (10 mL×2), 5% aqueous KHSO4 (10 mL) and finally with brine (10 mL)
  13. dry with materialto drying over Na2SO4
  14. customThe volatiles were removed
  15. customthe resulting oil was purified by preparative TLC

Sources & evidence

ORD record
ord-c551d55a8d064c4abb5f5900a449dd5c
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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