Trifluoroacetic acid → HCID 51354736, compound

HRID 1874630Notes

Reaction equation

HRID 1874630 reaction equation
[CH3:1][CH:2]([CH2:39][CH2:40][CH3:41])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])[CH2:12][NH:13][CH2:14][C:15]2([NH:20]C(=O)OC(C)(C)C)[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:20][C:15]1([CH2:14][NH:13][CH2:12][C@H:11]([NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH:2]([CH3:1])[CH2:39][CH2:40][CH3:41])=[CH:6][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67439252HCID 67439252, compound

Product 1

HCID 51354736HCID 51354736, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude t-butyl 1-(((2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethylamino)methyl)cyclopentylcarbamate from Part A (195 mg, 0.345 mmol) in dichloromethane (2 mL) at 0° C. was added TFA (1 mL, 12.98 mmol). The reaction mixture was stirred for 1.5 h while being allowed to warm to room temperature. The mixture was concentrated and the product was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA). The organic solvent was removed on the rotovapor and the aqueous mixture was frozen and placed on the lyophilizer to afford (2S)-N-((1R)-2-((1-aminocyclopentyl)methylamino)-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (154 mg, 63% yield, 2 steps) as a colorless amorphous solid: 1H NMR (300 MHz, 100° C., DMSO-d6) δ 7.95 (d, J=8.1 Hz, 1H), 7.16-7.34 (m, 5H), 7.11 (d, J=8.4 Hz, 2H), 6.81 (d, J=8.8 Hz, 2H), 6.87 (br. s., 5H), 4.94-5.06 (m, 1H), 3.68-3.88 (m, 3H), 2.96-3.13 (m, 2H), 2.93 (s, 2H), 1.59-1.95 (m, 9H), 1.40 (d, J=7.0 Hz, 3H), 1.17-1.49 (m, 4H), 0.97 (d, J=7.0 Hz, 3H), 0.90 (t, J=7.0 Hz, 3H); HPLC tR=2.68 min (Method A); LRMS (ESI) m/e 466.5 [(M+H)+, calcd for C29H44N3O2 466.4].

Workup

  1. concentrationThe mixture was concentrated
  2. customthe product was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA)
  3. customThe organic solvent was removed on the rotovapor
  4. temperaturethe aqueous mixture was frozen

Sources & evidence

ORD record
ord-741becdf5bce436e9527af706e83441c
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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