Trifluoroacetic acid → HCID 178511745, compound

HRID 243085Notes

Reaction equation

HRID 243085 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([O:12][C@H:10]1[CH2:11][C@H:8]([NH2:7])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454132HCID 178454132, compound

Product 1

HCID 178511745HCID 178511745, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (trans-3-benzyloxycyclobutyl)carbamic acid tert-butyl ester (0.99 g, 3.56 mmol) in DCM (10 mL) was added TFA (2 mL) and the mixture stirred at RT for 3 h. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and loaded onto an SCX-2 (20 g) cartridge. The cartridge was washed with DCM then MeOH and then 2M NH3 in MeOH solution. The relevant fractions were concentrated in vacuo to afford the title compound as yellow oil (0.6 g, quantitative). 1H NMR (CDCl3, 400 MHz): δ 7.36-7.31 (5H, m), 4.40 (2H, s), 4.29-4.20 (1H, m), 3.75-3.65 (1H, m), 2.39-2.26 (2H, m), 2.02-1.90 (2H, m), 1.49 (2H, s, br).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue dissolved in DCM
  3. washThe cartridge was washed with DCM
  4. concentrationThe relevant fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-eed626f9c10a4e3ea3ec4136360b2e9f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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