Methanol → HCID 131734121, compound
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- distillationThereafter, the solvent was distilled away under reduced pressure, and 20 mL of ethyl acetate and 20 mL of water
- additionwere then added to the obtained residue
- washwas then washed with water twice
- distillationThe solvent was distilled away under reduced pressure
Sources & evidence
- ORD record
- ord-bbef72a4eda04cdd9b463d11681fc0f9
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221865B2
Reaction notes
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