2,3-Dimethylbenzoic acid → 2(S)-Benzyl-1-tert-butoxycarbonyl-4-(1-naphthoyl)piperazine

HRID 342120Notes

Reaction equation

HRID 342120 reaction equation
[CH2:1]([C@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=O.[CH:32]1C=CC2N(O)N=NC=2[CH:37]=1.CCN=C=NCCCN(C)C.Cl>C(N(CC)CC)C>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:24]([C:23]2[C:22]3[C:30](=[CH:31][CH:32]=[CH:37][CH:21]=3)[CH:29]=[CH:28][CH:27]=2)=[O:26])[CH2:11][CH2:10][N:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylate

Product 1

HCID 229410392(S)-Benzyl-1-tert-butoxycarbonyl-4-(1-naphthoyl)piperazine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound was prepared according to the procedure described for Example 1, Step A except using 2(S)-benzyl-1-tert-butoxycarbonylpiperazine (0.292 g, 1.06 mmol), 2,3-dimethylbenzoic acid (0.159 g, 1.06 mmol), HOBT (0.157 g, 1.02 mmol), EDC.HCl (0.213 g, 1.11 mmol) and triethylamine to adjust the pH to 7. The title compound was obtained as a thick oil. 1HNMR (DMSO-d6, 300 MHz) δ 7.15 (2H, m), 6.06 (1H,m), 4.42 (1H,m), 3.6-4.2 (2H, m), 2.7-3.24 (4H, m), 2.24 (3H, s), 2.03-2.20 (3H, 4s), 1.10-1.6 (15H, m), 0.72-1.00 (3H, m).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-1946a6843071473195bbfb72a95fce80
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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