Methanol → HCID 131734121, compound

HRID 716148Notes

Reaction equation

HRID 716148 reaction equation
Cl.[CH3:2][O:3][NH2:4].[CH2:5]([O:12][C@:13]1([CH3:36])[C@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:15][C@@H:14]1O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CO>C(N(CC)CC)C>[CH2:28]([O:27][CH2:26][C@@H:16]([OH:15])[C@@H:17]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@@:13]([O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH:36]=[N:4][O:3][CH3:2])[CH3:14])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118108846HCID 118108846, compound

Product 1

HCID 131734121HCID 131734121, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.69 g of O-methylhydroxylamine hydrochloride was added to a mixture of 2.0 g of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyloxolan-2-ol and 10 mL of methanol, and thereafter, 0.56 g of triethylamine was added dropwise to the mixture. The obtained mixture was stirred at room temperature for 6 hours. Thereafter, the solvent was distilled away under reduced pressure, and 20 mL of ethyl acetate and 20 mL of water were then added to the obtained residue. The organic layer was fractionated, and was then washed with water twice. The solvent was distilled away under reduced pressure, so as to obtain 2.0 g of (2R,3R,4S)-1,3,4-tris(benzyloxy)-4-((methoxyimino)methyl)pentan-2-ol in the form of a colorless oily product.

Workup

  1. distillationThereafter, the solvent was distilled away under reduced pressure, and 20 mL of ethyl acetate and 20 mL of water
  2. additionwere then added to the obtained residue
  3. washwas then washed with water twice
  4. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-78c21178c16f42a0908f3b5485a4a2da
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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