Trifluoroacetic acid → HCID 44118830, compound

HRID 1441243Notes

Reaction equation

HRID 1441243 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH:13]2[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:15]1[CH2:16][CH:13]([CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45072305tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-1-carboxylate

Product 1

HCID 44118830HCID 44118830, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-azetidinecarboxylate (17.2 mmoles, 5.5 g) in DCM (100 mL) at RT was added TFA (50 mL). After 2 h, the reaction solution was concentrated under vacuum and purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) to give the title compound (3.59 g, 95%) as a light yellow oil: LC-MS (ES) m/e 221 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. custompurified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-7f3458304b6644589adc03924981bed1
Source dataset
uspto-grants-2010_02
Patent number
US07655648B2

Reaction notes

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