Trifluoroacetic acid → HCID 67303976, compound

HRID 1009874Notes

Reaction equation

HRID 1009874 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:51]=[CH:50][C:14]([CH2:15][C:16]2[C:17]([CH3:49])=[CH:18][C:19]([O:45][C:46](=[O:48])[CH3:47])=[C:20]([C@@H:22]3[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]3[O:24][C:25](=[O:27])[CH3:26])[CH:21]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]2[C:17]([CH3:49])=[CH:18][C:19]([O:45][C:46](=[O:48])[CH3:47])=[C:20]([C@@H:22]3[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]3[O:24][C:25](=[O:27])[CH3:26])[CH:21]=2)=[CH:50][CH:51]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67304729HCID 67304729, compound

Product 1

HCID 67303976HCID 67303976, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a chloroform solution (80 mL) of (1S)-1-[5-[4-(2-tert-butoxycarbonylaminoethyl)benzyl]-2-acetoxy-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-acetyl-D-glucitol was added trifluoroacetic acid (23 mL), and the mixture was stirred for 1.5 hours at room temperature. The solvent was evaporated under reduced pressure to obtain a residue. Thus obtained residue was diluted with chloroform, and washed with a saturated sodium bicarbonate aqueous solution and brine. This solution was dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain the title compound (4.67 g, quant.) as a colorless powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto obtain a residue
  3. washwashed with a saturated sodium bicarbonate aqueous solution and brine
  4. dry with materialThis solution was dried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0dd24676e33b450694dc37254e2026e0
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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