Hydrochloric Acid → (2S,3R,4R,5S,6R)-2-[4-cyclopropyl-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

HRID 1695867Notes

Reaction equation

HRID 1695867 reaction equation
C([N:8]1[C:13]2[CH:14]=[C:15]([CH2:18][C:19]3[CH:24]=[C:23]([C@H:25]4[C@H:30]([O:31]CC5C=CC=CC=5)[C@@H:29]([O:39]CC5C=CC=CC=5)[C@H:28]([O:47]CC5C=CC=CC=5)[C@@H:27]([CH2:55][O:56]CC5C=CC=CC=5)[O:26]4)[CH:22]=[CH:21][C:20]=3[CH:64]3[CH2:66][CH2:65]3)[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.Cl.CO>C1COCC1.[Pd]>[CH:64]1([C:20]2[CH:21]=[CH:22][C:23]([C@H:25]3[C@H:30]([OH:31])[C@@H:29]([OH:39])[C@H:28]([OH:47])[C@@H:27]([CH2:55][OH:56])[O:26]3)=[CH:24][C:19]=2[CH2:18][C:15]2[CH:16]=[CH:17][C:12]3[O:11][CH2:10][CH2:9][NH:8][C:13]=3[CH:14]=2)[CH2:66][CH2:65]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 529135264-benzyl-6-[2-cyclopropyl-5-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 52913527(2S,3R,4R,5S,6R)-2-[4-cyclopropyl-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triolYield 16.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyl-6-[2-cyclopropyl-5-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-3,4-dihydro-2H-benzo[1,4]oxazine (0.42 g, 0.4783 mmol) in THF (4.7 mL) was added 10% palladium on charcoal (80 mg), 0.1 mL conc. HCl followed by methanol (4.7 mL) and the mixture was stirred under hydrogen atmosphere for 18 h. The reaction mixture was filtered through a celite bed, washed with methanol and concentrated. The resulting residue was purified by preparative HPLC to furnish (2S,3R,4R,5S,6R)-2-[4-cyclopropyl-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (34 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed
  2. washwashed with methanol
  3. concentrationconcentrated
  4. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3f9881326b8149e7b1fa65852695a9e1
Source dataset
uspto-grants-2012_04
Patent number
US08163704B2

Reaction notes

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