Trifluoroacetic acid → 3-((S)-1-amino-3-cyclohexylpropan-2-ylamino)-4-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione

HRID 2355347Notes

Reaction equation

HRID 2355347 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]2[C:22](=[O:23])[C:21](=[O:24])[C:20]=2[N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[F:44])[O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH2:26]2)[CH2:9][NH:10]C(=O)OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:10][CH2:9][C@@H:8]([NH:18][C:19]1[C:22](=[O:23])[C:21](=[O:24])[C:20]=1[N:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[F:44])[O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH2:26]1)[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57544930tert-butyl (2S)-3-cyclohexyl-2-(2-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)propylcarbamate

Product 1

HCID 575447393-((S)-1-amino-3-cyclohexylpropan-2-ylamino)-4-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dioneYield 60%

Procedure

tert-butyl (2S)-3-cyclohexyl-2-(2-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)propylcarbamate (17.4 mg, 0.03 mmol) was treated with neat TFA for 30 min. TFA was removed in vacuo, and the residue was purified by HPLC to give 3-((S)-1-amino-3-cyclohexylpropan-2-ylamino)-4-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione (8.7 mg, 60%) as a TFA salt. 1H NMR (CD3OD) δ 0.8-2.1 (20H), 3.0 (1H), 3.1 (1H), 3.25 (s, 3H), 3.3 (m, 6H), 3.5 (2H), 4.45 (d, 1H), 4.63 (m, 1H), 7.15 (1H), 7.21 (1H), 7.35 (1H), 7.40 (1H). MS ESI+ve m/z 516 (M+1).

Workup

  1. customTFA was removed in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-4470c76beb6b4e8da5eadaf11a01f774
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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