Trifluoroacetic acid → N-Carbobenzoxysarcosine

HRID 485085

Reaction equation

HRID 485085 reaction equation
O1CCN[C:2]1=O.[C:7]([NH:17][CH2:18][C:19]([OH:21])=[O:20])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[C:7]([N:17]([CH2:18][C:19]([OH:21])=[O:20])[CH3:2])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14349BenzyloxycarbonylglycineHCID 739492-Oxazolidinone

Product 1

HCID 97053N-CarbobenzoxysarcosineYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The oxazolidinone from Cbz-glycine (221 mg, 1.0 mmole) was dissolved in 10 ml of CHCl3 and triethylsilane (193 ∥l=174 mg, 1.5 mmoles) and trifluoroacetic acid (770 μl, 10 mmoles) were added. The solution was stirred at room temperature for 2 hrs. and concentrated in vacuo. CHCl3 was added and the solution was reconcentrated to a colorless oil. Silica gel chromatography gave 107 mg (48%) of Cbz-sarcosine, identified by NMR (N-Me, 2.98 ppm) and amino acid analysis.

Workup

  1. concentrationand concentrated in vacuo
  2. additionCHCl3 was added

Sources & evidence

ORD record
ord-9817e6cc60184ba48a7cc56b80e3695f
Source dataset
uspto-grants-1985_08
Patent number
US04535167

Linked notes

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