Water → HCID 86659128, compound

HRID 1260396Notes

Reaction equation

HRID 1260396 reaction equation
C([O-])(=O)C.[Na+].[N-:6]=[N+:7]=[N-:8].[Na+].[CH3:10][C:11]([O:14][C:15]([NH:17][C@@H:18]1[C@@H:23](OS(C)(=O)=O)[CH2:22][CH2:21][O:20][CH2:19]1)=[O:16])([CH3:13])[CH3:12].O>CN(C=O)C.C(OCC)(=O)C>[N:6]([C@@H:23]1[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]1[NH:17][C:15](=[O:16])[O:14][C:11]([CH3:12])([CH3:10])[CH3:13])=[N+:7]=[N-:8]

Participants

7

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 86659127HCID 86659127, compound

Product 1

HCID 86659128HCID 86659128, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

Sodium acetate (129 g), sodium azide (102 g) and 1,5-anhydro-2,4-dideoxy-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-O-(methylsulfonyl)-L-threo-pentitol (232 g) were mixed in DMF (1 l) and stirred and heated at 95° C. for 6 h. Water (2 l) was added and the mixture thoroughly mixed, ethyl acetate 1.5 l) was added and the mixture stirred for 5 min. The phases were separated, the aqueous extracted with ethyl acetate (1 l), the combined organics washed with water (2×2 l), dried and reduced to dryness in vacuo to give 1,1-dimethylethyl [(3R,4R)-4-azidotetrahydro-2H-pyran-3-yl]carbamate (153 g).

Workup

  1. additionthe mixture thoroughly mixed
  2. stirringthe mixture stirred for 5 min
  3. customThe phases were separated
  4. extractionthe aqueous extracted with ethyl acetate (1 l)
  5. washthe combined organics washed with water (2×2 l)
  6. customdried

Sources & evidence

ORD record
ord-f373f0477a4747059ddbbbc6fa1c4b31
Source dataset
uspto-grants-2013_06
Patent number
US08470835B2

Reaction notes

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