Hydrochloric Acid → HCID 52914725, compound

HRID 1944088Notes

Reaction equation

HRID 1944088 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:50][OH:51])[CH2:48][OH:49])C1C=CC=CC=1.Cl>CO.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:12]2[O:11][C:10]([CH2:50][OH:51])([CH2:48][OH:49])[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@H:13]2[OH:23])=[CH:32][C:33]=1[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([O:45][CH2:46][CH3:47])=[CH:43][CH:44]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52914724HCID 52914724, compound

Product 1

HCID 52914725HCID 52914725, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {(3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-tetrahydro-pyran-2-yl}-methanol (125 mg, 0.16 mmole) in methanol (3 mL), 10% Pd/C (65 mg) and 2 drops of con. HCl were added and stirred under hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered through cetlie bed, washed with methanol (20 mL). The crude product was purified by preparative HPLC to furnish 25 mg of (3S,4R,5R,6S)-6-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-bis-hydroxymethyl-tetrahydro-pyran-3,4,5-triol.

Workup

  1. filtrationThe reaction mixture was filtered through cetlie bed
  2. washwashed with methanol (20 mL)
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c696141f4ffe4ad9b74701abfbb87a6f
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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