Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-propylbenzoate → Benzyl 6-amino-2-methyl-3-propylbenzoate

HRID 1725917Notes

Reaction equation

HRID 1725917 reaction equation
C(OC([NH:8][C:9]1[C:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[C:13]([CH3:25])[C:12]([CH2:26][CH2:27][CH3:28])=[CH:11][CH:10]=1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][C:9]1[C:14]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[C:13]([CH3:25])[C:12]([CH2:26][CH2:27][CH3:28])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 68866397Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-propylbenzoate

Product 1

HCID 68862478Benzyl 6-amino-2-methyl-3-propylbenzoateYield 112.9%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of Example 148A (0.38 g, 1.0 mmol) in 4N HCl/dioxane was stirred at ambient temperature overnight and concentrated to provide the desired product (0.32 g, 100%). 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.40-1.52 (m, 2H), 2.16 (s, 3H), 2.22 (t, 2H), 5.34 (s, 2H), 7.11 (d, 1H), 7.30-7.50 (m, 5H); MS (ESI(+) m/e 284 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-385cbe5454c6463f8b0320d0a54c5f43
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…