HCID 57544689, compound → HCID 57544599, compound

HRID 2355356Notes

Reaction equation

HRID 2355356 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([NH:23][C@@H:24]([CH2:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)=[O:22])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]>Cl.O1CCOCC1>[CH:36]1([CH2:35][C@H:24]([NH:23][C:21]([N:17]2[CH2:18][CH2:19][CH2:20][C@@H:15]([C@H:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:7][CH2:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:16]2)=[O:22])[CH2:25][NH:26][CH3:27])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

3

Reactant 1

HCID 57544689HCID 57544689, compound

Product 1

HCID 57544599HCID 57544599, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

tert-butyl (S)-2-((S)-3-((R)-5-ethoxy-1-phenylpentyl)piperidine-1-carboxamido)-3-cyclohexylpropylmethylcarbamate (40.7 mg, 0.071 mmol) was stirred in HCl/dioxane (4 N, 4 mL) at rt until no starting material remained. The solvent was removed to give (3S)—N—((S)-3-cyclohexyl-1-(methylamino)propan-2-yl)-3-((R)-5-ethoxy-1-phenylpentyl)-piperidine-1-carboxamide (32.9 mg, 91%) as its HCl salt. 1H NMR (CD3OD) δ 0.9 (m, 3H), 1.0 (m, 2H), 1.11 (t, 3H), 1.2-2.0 (20H), 2.40 (m, 1H), 2.65 (m, 1H), 2.70 (s, 3H), 3.93 (m, 1H), 3.05 (m, 2H), 3.31 (m, 1H), 3.40 (q, 2H), 3.91 (d, 1H), 4.13 (m, 2H), 7.13 (2H), 7.19 (1H), 7.28 (2H). MS ESI+ve m/z 472 (M+1).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-c3790ca8d83c4a3a9d131385cfab6037
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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