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 1258861Notes

Reaction equation

HRID 1258861 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-df2dd908c44848b0a585113f161d7ba2
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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