Trifluoroacetic acid → HCID 67642579, compound

HRID 1597764Notes

Reaction equation

HRID 1597764 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6](=[O:28])[CH:7]([OH:27])[CH:8]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(F)(F)C(O)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6](=[O:28])[C:7](=[O:27])[CH:8]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 67641967HCID 67641967, compound

Product 1

HCID 67642579HCID 67642579, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-hydroxy-6-phenyl-5-[((phenylmethoxy)carbonyl)amino]-3-oxohexanoic acid ethyl ester (397 mg, 1.0 mmol) is dissolved in acetonitrile (15 ml) and the Dess-Martin periodinane (1.27 g, 3.0 mmol)) is added. To the mixture trifluoroacetic acid (342 mg, 3.0 mmol) is added and the mixture is stirred for 48 h. The solvent is removed in vacuo and EtOAc (100 ml) is added, followed by the addition of a solution of NaHCO3 (0.80 g) and Na2S2O3 (1.41 g) in H2O (25 ml). The organic layer is separated and the aqueous phase extracted with ethyl acetate. The combined extracts are dried over Na2S2O3 and the solvent is removed in vacuo. The product is purified by flash chromatography on silica gel.

Workup

  1. customThe solvent is removed in vacuo and EtOAc (100 ml)
  2. additionis added
  3. additionfollowed by the addition of a solution of NaHCO3 (0.80 g) and Na2S2O3 (1.41 g) in H2O (25 ml)
  4. customThe organic layer is separated
  5. extractionthe aqueous phase extracted with ethyl acetate
  6. dry with materialThe combined extracts are dried over Na2S2O3
  7. customthe solvent is removed in vacuo
  8. customThe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-37af870ddf6447d395fe4de0c828791b
Source dataset
uspto-grants-1998_04
Patent number
US05736520

Reaction notes

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