Water → HCID 57003423, compound

HRID 2269352Notes

Reaction equation

HRID 2269352 reaction equation
[OH-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][N:10]1[C@@H:13]([CH3:14])[C@@H:12]([CH2:15][CH:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[C:11]1=[O:28].O.S([O-])(O)(=O)=[O:31].[Na+]>O1CCOCC1.CCOC(C)=O>[C:22]1([CH:19]2[CH2:20][CH2:21][CH:16]([CH2:15][C@H:12]([C@@H:13]([NH:10][O:9][CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][O:3]3)[CH3:14])[C:11]([OH:28])=[O:31])[CH2:17][CH2:18]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium Hydroxide2×HCID 516919Sodium BisulfateHCID 56987650HCID 56987650, compound

Product 1

HCID 57003423HCID 57003423, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3 N sodium hydroxide (18.7 mL) is added dropwise to a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-(4-phenylcyclohexylmethyl)-4-methylazetidin-2-one (3.6 g, 0.010 mol) in dioxane (50 mL) at 25° C. and the mixture is stirred for 18 h. Water (10 mL) is added to the reaction mixture and an additional 5 mL of 3 N sodium hydroxide is added dropwise and the mixture is stirred an additional 8 h. The reaction mixture is mixed with water (200 mL), 1 M sodium hydrogen sulfate (60 mL) and EtOAc (100 mL). The aqueous phase is extracted with EtOAc. The combined organic phase is washed with water and saturated sodium chloride solution, dried (sodium sulfate) and concentrated in vacuo to give 3.44 g (92%) of (2R,3S)-2-(4-phenylcyclohexylmethyl)-3-(2-tetrahydropyranyloxyamino)butanoic acid as a white solid. The product is used without further purification:

Workup

  1. stirringthe mixture is stirred an additional 8 h
  2. extractionThe aqueous phase is extracted with EtOAc
  3. washThe combined organic phase is washed with water and saturated sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06d84fde31584b10bac11ac1a3264560
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

Loading…