Methanol → (2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-azido-2-hydroxyheptanamide

HRID 1698428Notes

Reaction equation

HRID 1698428 reaction equation
CO.[OH:3][C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:10][C:11]([C@@H:13]1[C@@H:15]([CH2:16][CH2:17][CH2:18][CH3:19])[O:14]1)=[O:12].[N-:20]=[N+:21]=[N-:22].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O>[OH:3][C@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:10][C:11](=[O:12])[C@@H:13]([OH:14])[C@@H:15]([N:20]=[N+:21]=[N-:22])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 33557Sodium AzideHCID 86618962(2S)-trans-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-butyloxiranecarboxamide

Product 1

HCID 59655568(2S,3S)-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-azido-2-hydroxyheptanamideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 ml of a methanol suspension containing 1.64 g (7 mmol) of (2S)-trans-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-butyloxiranecarboxamide, 910 mg (14 mmol) of sodium azide and 868 mg (7.2 mmol) of anhydrous magnesium sulfate was refluxed for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the reaction mixture was poured into 300 ml of water and the resulting mixture was stirred for 2 hours. The resulting crystals were collected by filtration and washed with water, and dried to obtain 1.45 g (Yield: 73%) of the title compound.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customwas returned to room temperature
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2bb56db98e2d403fba159f85dfdcd781
Source dataset
uspto-grants-2012_04
Patent number
US08163943B2

Reaction notes

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