Trifluoroacetic acid methylene chloride → (3r)-3-((r)-(3-Methoxypropoxy)(phenyl)methyl)-n-((s)-1-amino-3-cyclohexylpropan-2-yl)piperidine-1-carboxamide trifluoroacetic acid salt

HRID 2355352Notes

Reaction equation

HRID 2355352 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([NH:16][C@@H:17]([CH2:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:18][NH:19]C(=O)OCC[Si](C)(C)C)=[O:15])[CH2:9]1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].C(Cl)Cl>>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([NH:16][C@@H:17]([CH2:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:18][NH2:19])=[O:15])[CH2:9]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 866261922-(Trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropylcarbamate

Product 1

HCID 67192707(3r)-3-((r)-(3-Methoxypropoxy)(phenyl)methyl)-n-((s)-1-amino-3-cyclohexylpropan-2-yl)piperidine-1-carboxamide trifluoroacetic acid salt

Procedure

2-(Trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carboxamido)-3-cyclohexylpropylcarbamate (85.3 mg, 0.14 mmol) was dissolved in 6 mL 1:1 TFA/CH2Cl2 (6 mL) and stirred for 30 min. LC-MS showed the reaction was complete. After concentration, (3R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)-N—((S)-1-amino-3-cyclohexylpropan-2-yl)piperidine-1-carboxamide trifluoroacetic acid salt was isolated by prep HPLC. LC-MS (3 min) tR=1.56 min, m/z 446 (M+1). 1H NMR (CD3OD) δ 7.37-7.25 (m, 5H), 4.30 (d, 1H), 4.03 (m, 1H), 4.97-4.90 (m, 2H), 3.50-3.39 (m, 2H), 3.27 (s, 3H), 3.00 (dd, 1H), 2.85-2.75 (m, 3H), 1.81-0.82 (m, 22H).

Workup

  1. concentrationAfter concentration

Sources & evidence

ORD record
ord-047bdf8f857d4e59bc23484d8494797a
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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