Phenyl chloroformate → HCID 86690207, compound

HRID 2369978Notes

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:32])[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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:32])[O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 15891Phenyl chloroformate

HCID 71233239HCID 71233239, compound2×

Product 1

HCID 86690207HCID 86690207, compound

Procedure

Phenyl (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 phenyl carbonochloridate (14.75 mg, 0.094 mmol) according to General Procedure G to give 5 mg (10% yield) of the product as a yellow solid. Anal. Calcd. for C24H30N4O4 m/z 438.5, found: 439.4 (M+H)+; 1H NMR (500 MHz, MeOH-d3) δ ppm 8.09 (d, J=9.3 Hz, 2H), 7.26 (t, J=8.0 Hz, 2H), 7.17 (d, J=7.7 Hz, 1H), 7.11-7.05 (m, 2H), 6.90 (d, J=7.7 Hz, 1H), 3.86 (d, J=13.2 Hz, 1H), 3.68-3.55 (m, 3H), 3.47-3.36 (m, 2H), 3.26-3.19 (m, 1H), 2.29 (br. s., 1H), 2.21-2.15 (m, 1H), 2.10 (br. s., 1H), 1.99-1.74 (m, 5H), 1.62-1.36 (m, 4H); 13C NMR (126 MHz, MeOH-d3) δ ppm 156.21, 140.60, 129.95, 126.33, 126.25, 122.30, 121.96, 115.57, 115.10, 61.27, 54.06, 52.88, 50.25, 49.28, 32.42, 29.24, 28.01, 24.92, 24.37, 22.67.

Sources & evidence

ORD record: ord-ffb677c25d2844909d7af0fdba949a87
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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