Benzyl chloroformate → HCID 71488631, compound

HRID 2369977Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH2:23])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:24](Cl)(=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@H:12]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 71233239HCID 71233239, compound2×

Product 1

HCID 71488631HCID 71488631, compound

Procedure

Benzyl (1R,2R)-2-((S)-1-(4-nitrophenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using (1R,2R)—N1-(1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (from intermediate C, Example 2) (30 mg, 0.094 mmol) and benzyl carbonochloridate (16.07 mg, 0.094 mmol) according to General Procedure G to give 5 mg (12% yield) of the product as a yellow solid. Anal. Calcd. for C25H32N4O4 m/z 452.5, found: 453.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 8.08 (d, J=9.3 Hz, 2H), 7.36-7.29 (m, 5H), 6.77 (d, J=9.3 Hz, 2H), 5.05 (br. s., 2H), 4.91 (br. s., 1H), 3.75 (d, J=10.4 Hz, 1H), 3.66 (d, J=12.6 Hz, 1H), 3.31 (d, J=7.7 Hz, 1H), 3.04 (t, J=10.7 Hz, 1H), 2.83 (br. s., 2H), 2.54 (br. s., 1H), 2.15-2.03 (m, 2H), 1.99-1.91 (m, 1H), 1.83 (dd, J=9.1, 4.7 Hz, 2H), 1.79-1.69 (m, 3H), 1.32 (d, J=8.8 Hz, 2H), 1.48 (br. s., 1H), 1.62 (ddd, J=13.9, 10.4, 10.3 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 156.63, 154.71, 136.37, 128.52, 128.14, 126.12, 112.77, 66.77, 59.06, 50.93, 47.94, 32.19, 29.68, 24.53, 23.07.

Sources & evidence

ORD record: ord-114044549be644c78b9c2ebc1149b332
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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