2,3-Dimethylbenzoic acid → 1-tert-Butoxycarbonyl-4-(2,3-dimethylbenzoyl)-2(S)-(2-methoxyethyl)piperazine

HRID 1598450Notes

Reaction equation

HRID 1598450 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:14][CH2:15][O:16][CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:27]([CH3:28])[C:19]=2[CH3:18])[CH2:10][C@@H:9]1[CH2:14][CH2:15][O:16][CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15406047(S)-Tert-butyl 2-(2-methoxyethyl)piperazine-1-carboxylate

Product 1

HCID 228841481-tert-Butoxycarbonyl-4-(2,3-dimethylbenzoyl)-2(S)-(2-methoxyethyl)piperazineYield 80.8%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the procedure described for Example 1, Step A except using 1-tert-butoxycarbonyl-2(S)-(2-methoxyethyl)piperazine (0.179 g, 0.73 mmol), 2,3-dimethylbenzoic acid (0.115 g, 0.75 mmol), HOBT (0.098 g, 0.73 mmol), EDC.HCl (0.153 g, 0.80 mmol) in methylene chloride (5 mL). Triethylamine was added to adjust the pH to 7. Chromatography on silica gel with 40% ethyl acetate in hexane afforded the title compound as a clear oil (0.222 g). NMR (CDCl3, 300 MHz) δ 6.9-7.2 (5H, m), 4.70 (1H, m), 3.8-4.5 (9H, mm), 2.0-2.3 (6H, mm), 1.9 (2H, m), 1.59 (9H, s).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ecbd0322f6ff4aef950089643323610f
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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