Реакция #219468

Уравнение реакции

Trifluoroacetic acid

2-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester

dichloromethane

→

desired product

Выход 99.0%

2-(S)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester

Выход 99.0%

Условия реакции

Обработка

1. 1
   ДругоеReaction mixture
2. 2
   КонцентрированиеMixture was concentrated in vacuo
3. 3
   workup.DISSOLUTIONResidue was dissolved in dichloromethane (75 mL)
4. 4
   Промывкаwashed successively with saturated aqueous sodium bicarbonate (2×50 mL) and brine (30 mL)
5. 5
   СушкаOrganic was dried (magnesium sulfate)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated in vacuo

Методика

Trifluoroacetic acid (10 mL) was added to a solution of 2-(S)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester (4.6 g, 9.9 mmol) in dichloromethane (40 mL). Reaction mixture was stirred at room temperature for 1.5 hours. Mixture was concentrated in vacuo. Residue was dissolved in dichloromethane (75 mL) and washed successively with saturated aqueous sodium bicarbonate (2×50 mL) and brine (30 mL). Organic was dried (magnesium sulfate), filtered and concentrated in vacuo to yield the desired product in 99% yield as an amber oil. 1H NMR (300 MHz, CDCl3): δ=6.85 (d, J=8.1, 1H), 6.67 (d, J=8.4, 1H), 5.18 (m, 2H), 4.09 (m, 4H), 3.09 (dd, J1=6.2, J2=13.9, 1H), 2.96 (m, 1H), 2.66 (m, 2H), 2.37 (dd, J1=4.6, J2=16.7, 1H), 2.15 (s, 3H), 2.06 (s, 3H), 1.20 (m, 6H). MS m/e (M−C2H4O2+H)+=306.2.

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