Ammonia → HCID 86718422, compound

HRID 2204047Notes

Reaction equation

HRID 2204047 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[CH:16]=2)[O:8]/[C:7](=[N:32]\[OH:33])/[C@H:6]1[O:34]C(=O)C)(=O)C.N>CO>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@H:9]2[O:8][C:7](=[N:32][OH:33])[C@@H:6]([OH:34])[C@H:5]([OH:4])[C@H:10]2[OH:11])=[CH:16][C:17]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 87190441HCID 87190441, compound

Product 1

HCID 86718422HCID 86718422, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound from step B (97 mg, 0.18 mmol) was treated with 7.0 M NH3 in MeOH (1.8 ml) for 1 hour. The reaction was concentrated under vacuum, and the residue was purified by flash chromatography (12 g SiO2, 0-12% MeOH:CH2Cl2), suspended in H2O, and lyophilized to give (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-one oxime (57 mg, 0.14 mmol, 77%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue was purified by flash chromatography (12 g SiO2, 0-12% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-f112eebd4c9d47a48f4144182e7c15b0
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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