Triethylamine → 2-(tert-butoxycarbonyl)amino-5-isopropyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362917Notes

Reaction equation

[CH:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=O)[C:7]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[NH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.O>[C:17]([O:16][C:14]([NH:13][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:12][C:8]=1[C:9]([NH:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:25][CH2:24]1)=[O:11])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Step 3): A mixture of 5-isopropyl-N-tert-butoxycarbonylanthranilic acid (1.0 g, 3.58 mmol), 4-aminomethyl-1-diphenylmethylpiperidine (1.0 g, 3.57 mmol), triethylamine (0.37 g, 3.66 mmol) and DPPA (1.0 g, 3.63 mmol) in DMF was stirred at 0° C. for 30 mins and at room temperature for 2 hours. The mixture was poured into H2O and extracted with AcOEt. The extract was washed with H2O, dried over MgSO4 and evaporated and then the residue was purified by column chromatography on silica gel to give 2-(tert-butoxycarbonyl)amino-5-isopropyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide, 1.86 g (96.4%): mp 88°-90° C.

Workup

extractionextracted with AcOEt
washThe extract was washed with H2O
dry with materialdried over MgSO4
customevaporated
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-0360362680714b75873f927ddd8e067a
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872115

Reaction notes

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