Benzyl chloroformate → HCID 18991271, compound

HRID 375788Notes

Reaction equation

HRID 375788 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([O-:6])=[O:5].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(O)=O.[Rh]>[C:21]([NH:1][CH:2]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([OH:6])=[O:5])([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 22146734HCID 22146734, compound

Product 1

HCID 18991271HCID 18991271, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 25 g (151 mmol) of 3-amino-3-phenylproprionate in 450 mL of HOAc was charged with 25 g of 5% Rh/Al2O3 and the mixture hyrogenated at 60 psi for 30 hr at 60° C. The reaction was filtered over celite and evaporated in vacuo to a dark oil. The presence of the desired product was confirmed by FD-MS (m/e 172, MH+, 100). The crude reduction product was treated with benzylchloroformate (25.67 g; 151 mmol) under basic conditions substantially according to the procedures of Example 1, A, to afford 23.4 g of N-Cbz-3-amino-3-cyclohexyl propionic acid as a grey solid.

Workup

  1. filtrationThe reaction was filtered over celite
  2. customevaporated in vacuo to a dark oil

Sources & evidence

ORD record
ord-b2ea368b62974e98859875205566091e
Source dataset
uspto-grants-1996_01
Patent number
US05488037

Reaction notes

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