Hydroxylamine → HCID 89852008, compound

HRID 627119Notes

Reaction equation

HRID 627119 reaction equation
[CH2:1]([O:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH:2]=[CH2:3].CC([O-])(C)C.[K+].[Si:19]([O:26][CH2:27][C@@H:28]1[CH:33]=[C:32]([CH2:34][O:35][CH3:36])[C@H:31](OS(C)(=O)=O)[CH2:30][N:29]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].ON>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]([C:6]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12])[C@H:31]1[CH2:30][N:29]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[C@H:28]([CH2:27][O:26][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:33]=[C:32]1[CH2:34][O:35][CH3:36])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 22322878Carbamic acid, (2-propenyloxy)-, 1,1-dimethylethyl ester (9CI)HCID 23665647Potassium tert-butoxideHCID 89852146(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-(methylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852008HCID 89852008, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl allyloxycarbamate (7.39 g, 42.66 mmol) in DMF (150 mL) at rt, potassium 2-methylpropan-2-olate (42.66 mL, 42.66 mmol) was added and gave a purple solution. After 30 min at rt, the mixture was cooled to 0° C. and (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(methoxymethyl)-5-(methylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (crude, 16.55 g, 35.55 mmol) in 50.0 mL DMF was added. The mixture was then warmed up to rt for 1 h. It was then diluted with ethyl acetate (200 mL) and washed aqueous sat. NaHCO3 solution, brine, dried over MgSO4, filtered and concentrated to give a residue which contains some starting material. The crude was purified on a silica gel column yielding a colorless oil. (19.3 g). 1HNMR shows still a mixture (with hydroxyamine starting material). It was used directly in TBS deprotection.

Workup

  1. customgave a purple solution
  2. temperatureThe mixture was then warmed up to rt for 1 h
  3. washwashed aqueous sat. NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue which
  8. customThe crude was purified on a silica gel column
  9. customyielding a colorless oil

Sources & evidence

ORD record
ord-bc5afb549ff4447999d02a7b4cd18350
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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