Benzyl chloroformate → HCID 10978298, compound

HRID 636023Notes

Reaction equation

HRID 636023 reaction equation
FC(F)(F)C([NH:5][C@@H:6]([C@H:10]([CH3:13])[CH:11]=[CH2:12])[C:7]([OH:9])=[O:8])=O.[OH-].[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O>[CH2:22]([O:21][C:19]([NH:5][C@@H:6]([C@H:10]([CH3:13])[CH:11]=[CH2:12])[C:7]([OH:9])=[O:8])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide3×HCID 11770121HCID 11770121, compound

Product 1

HCID 10978298HCID 10978298, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 25.16 g (112 mmol) of (2S,3R)-2-trifluoroacetylamino-3-methyl-4-pentenoic acid and 112 mL of 2 N aqueous sodium hydroxide is stirred at 80° C. for 1.5 h. The mixture is then allowed to cool to 25° C. and is further chilled to 0° C. 2 N aqueous sodium hydroxide (112 mL) is added followed by dropwise addition of 18 mL (126 mmol) of benzyl chloroformate. After 45 min at 0° C. and 5 h at 25° C. the mixture is added to 150 mL of water and is treated with aqueous sodium hydroxide until an orange solution resulted. The mixture is extracted with ether. The aqueous phase is acidified with 6 N HCl to pH 1 and is extracted with ether. Drying over magnesium sulfate and concentration in vacuo affords 22.61 g (77%) of (2S,3R)-2-benzyloxycarbonylamino-3-methyl-4-pentenoic acid as an oil.

Workup

  1. temperatureto cool to 25° C.
  2. temperatureis further chilled to 0° C
  3. waitAfter 45 min at 0° C.
  4. customresulted
  5. extractionThe mixture is extracted with ether
  6. extractionis extracted with ether
  7. dry with materialDrying over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-7a797558657e4bf69adc4d0cfc2ea364
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

Loading…