Benzyl succinimido carbonate → HCID 71226412, compound

HRID 2369992Notes

Reaction equation

HRID 2369992 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[CH2:10]1.[C:25](=O)([O:34]N1C(=O)CCC1=O)[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([O:26][C:25]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)[CH2:10]1)=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 71226920HCID 71226920, compound

Product 1

HCID 71226412HCID 71226412, compound

Procedure

Methyl 4-((S)-3-((1R,2R)-2-(benzyloxycarbonylamino)cyclohexylamino) piperidin-1-yl)benzoate was synthesized using methyl 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzoate (98 mg, 0.296 mmol) and benzyl 2,5-dioxopyrrolidin-1-yl carbonate (73.7 mg, 0.296 mmol) according to General Procedure H to give 38 mg (20% yield) of yellow solid. Anal. Calcd. for C27H35N3O4 m/z 465.5, found: 466.1 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.88 (d, J=9.0 Hz, 2H), 7.30-7.18 (m, 3H), 7.16-7.09 (m, 2H), 7.05 (d, J=8.9 Hz, 2H), 4.93 (s, 2H), 3.84 (s, 3H), 3.72-3.47 (m, 3H), 3.47-3.11 (m, 4H), 2.29 (d, J=13.4 Hz, 1H), 2.12-1.99 (m, 2H), 1.96-1.77 (m, 5H), 1.61-1.29 (m, 4H).

Sources & evidence

ORD record
ord-7a04791e3fe746d7b92a2bfd734f4f0e
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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