1-Hydroxybenzotriazole → HCID 58762215, compound

HRID 1453237Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1([C:20](=[O:26])[CH2:21][CH2:22][C:23](O)=[O:24])[CH2:19][CH2:18][CH2:17][CH2:16]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:23](=[O:24])[CH2:22][CH2:21][C:20]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (0.3 g, 1.49 mmol) in anhydrous CH2Cl2 under argon and cooled to 0° C., were added 4-Cyclopentyl-4-oxo-butyric acid (0.31 g, 1.79 mmol), EDC.HCl (0.35 g, 1.79 mmol), HOBt (0.24 g, 1.79 mmol), and TEA (0.25 mL, 1.79 mmol). The resulting solution was stirred at 25° C. overnight. CH2Cl2 was evaporate and the residue was partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O, brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (80% EtOAc in hexanes) to provide the desired product (0.37 g, 71%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.24-1.32 (m, 2H), 1.45 (s, 9H), 1.60-1.85 (m, 11H), 2.41 (t, J=6.4 Hz, 2H), 2.79-3.04 (m, 5H), 3.85-4.13 (m, 2H), 5.65 (s, 1H). MS(ESI):351 (MH−).

Workup

customCH2Cl2 was evaporate
customthe residue was partitioned between EtOAc and 1N HCl
washThe organic layer was washed with H2O, brine
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo
customthe residue was purified by flash column chromatography (80% EtOAc in hexanes)

Sources & evidence

ORD record: ord-4c793bcd1480495bbd92154c9f275381
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

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