Benzyl chloroformate → HCID 19878082, compound

HRID 1885753Notes

Reaction equation

HRID 1885753 reaction equation
[NH2:1][CH:2]([P:10]([OH:12])[OH:11])[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O1CCOCC1.[OH-].[Na+]>[C:14]([NH:1][CH:2]([P:10]([OH:12])[OH:11])[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 19878086HCID 19878086, compound

Product 1

HCID 19878082HCID 19878082, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 7.00 g (0.037 moles) of 1-amino-2-cyclohexylethylphosphonous acid in 105 ml of dioxane and 40 ml of 1N NaOH was cooled to 0° C. in an ice bath and stirred vigorously while 10.50 ml (12.53 g; 0.073 moles) of benzyl chloroformate and 80 ml of 1N NaOH were added rapidly and simultaneously over a period of approximately 1 minute. The pH was adjusted to the 8-9 range using 1N NaOH (hydrion paper) added in small increments. The reaction mixture was allowed to come to room temperature, and vigorous stirring was continued for 48 hours. The dioxane was removed in vacuo and the aqueous washed with 100 ml of ether. The ether layer was discarded and the aqueous solution acidified using 1N KHSO4 to approximately pH=1-2 (hydrion paper). The solution was extracted with 5×100 ml of ethyl acetate. The combined ethyl acetate layers were dried over anhydrous Na 2 SO4, filtered, and evaporated in vacuo to afford N-CBZ-1-amino-2-cyclohexylethylphosphonous acid as a white solid.

Workup

  1. additionwere added rapidly and simultaneously over a period of approximately 1 minute
  2. additionadded in small increments
  3. customto come to room temperature
  4. customThe dioxane was removed in vacuo
  5. washthe aqueous washed with 100 ml of ether
  6. extractionThe solution was extracted with 5×100 ml of ethyl acetate
  7. dry with materialThe combined ethyl acetate layers were dried over anhydrous Na 2 SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d08bd07b66554207b279325403404e2e
Source dataset
uspto-grants-1992_09
Patent number
US05145990

Reaction notes

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