Trifluoroacetic acid → HCID 54518252, compound

HRID 482249Notes

Reaction equation

HRID 482249 reaction equation
C(OC(=O)[CH:10]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:11]([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1.[CH3:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].FC(F)(F)[C:42](O)=[O:43]>CCOCC>[CH2:26]([O:25][C:23](=[O:24])[CH:10]([O:43][CH2:42][C:36]1[CH:35]=[CH:34][CH:39]=[CH:38][CH:37]=1)[C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 10503904HCID 10503904, compound

Product 1

HCID 54518252HCID 54518252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Then, 23.2 g of this 2-benzyloxycarbonyl-3(R)-t-butoxycarbonyl-5-methylhexanoic acid benzyl ester was dissolved in 75 ml of 95% trifluoroacetic acid aqueous solution and stirred overnight at room temperature. Trifluoroacetic acid was evaporated off in vacuo, the residue dissolved in 100 of methylene chloride, washed with saturated NaCl aqueous solution and dried over anhydrous magnesium sulfate. After concentration in vacuo, syrup thus obtained was dissolved in 70 ml of ether and, after addition of 200 ml of n-hexane, precipitated crystals were removed by filtration and the filtrate was concentrated in vacuo, yielding 12.5 g of 2-benzyloxy-3(R)-hydroxycarbonyl-5-methylhexanoic acid benzyl ester.

Workup

  1. customTrifluoroacetic acid was evaporated off in vacuo
  2. dissolutionthe residue dissolved in 100 of methylene chloride
  3. washwashed with saturated NaCl aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration in vacuo, syrup
  6. customthus obtained
  7. customprecipitated crystals
  8. customwere removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b427ddb317d1492dafaa2c204c5f1224
Source dataset
uspto-grants-1998_08
Patent number
US05795891

Reaction notes

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