Trifluoroacetic acid → (s)-[(4-Aminomethyl-cyclohexylmethyl)-amino]-phenyl-acetic acid cyclopentyl ester

HRID 548272Notes

Reaction equation

HRID 548272 reaction equation
[CH:1]1([O:6][C:7](=[O:32])[C@@H:8]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][NH:24]C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([O:6][C:7](=[O:32])[C@@H:8]([NH:15][CH2:16][CH:17]2[CH2:18][CH2:19][CH:20]([CH2:23][NH2:24])[CH2:21][CH2:22]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57971740(s)-{[4-(Tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-phenyl-acetic acid cyclopentyl ester

Product 1

HCID 57971691(s)-[(4-Aminomethyl-cyclohexylmethyl)-amino]-phenyl-acetic acid cyclopentyl esterYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-{[4-(tert-Butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-phenyl-acetic acid cyclopentyl ester (223 mg, 0.5 mmol) was stirred in DCM (4 ml), TFA (1 ml) was added and the mixture was stirred at r.t, for 2 h. The solution was concentrated in vacuo, taken up in DCM, washed twice with a saturated solution of NaHCO3 and once with a saturated solution of brine. The organic phase was dried over magnesium sulfate, filtered and evaporated to yield the expected amine as a yellow oil (130 mg, 75% yield). LCMS purity 100%, m/z 345 [M++H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed twice with a saturated solution of NaHCO3 and once with a saturated solution of brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7aa6bbbba6e54bd2aea828c442a4516a
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

Loading…