Water → HCID 57486903, compound

HRID 15363Notes

Reaction equation

HRID 15363 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@H:10]1[OH:25])=[O:7])([CH3:4])[CH3:3].[OH-].[Na+].S(OC)(O[CH3:32])(=O)=O.O>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:4][C:2]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@H:10]1[O:25][CH3:32])=[O:7])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 57486904HCID 57486904, compound2×

Product 1

HCID 57486903HCID 57486903, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-1-piperidinecarboxylate (for a synthesis, see WO2004058144, Example 5 (b) cis-4-tertbutoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester, Enantiomer 1) (2.2 g, 6.28 mmol) in THF (12 ml) was treated with 50% sodium hydroxide solution (12 ml), benzyltriethylammonium chloride (0.04 g) and dimethyl sulphate (1.31 g, 10.43 mmol) and stirred at RT for 60 hours. Water (100 ml) was added and the product was extracted with ethyl acetate (150 ml). The organic phase was separated and dried. Filtration and evaporation to dryness gave the title compound (2.2 g).

Workup

  1. extractionthe product was extracted with ethyl acetate (150 ml)
  2. customThe organic phase was separated
  3. customdried
  4. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-2cf2dce2d44e45fbab33c4a2f9a78f45
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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