反応 #1994332

反応方程式

benzyl [(1S)-1-benzyl-2-({(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl]carbamate

methanol

TFA

→

title compound

収率 90.0%

Benzyl [(1S)-2-(D-alanylamino)-1-benzylethyl]carbamate

収率 90.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   濃縮concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (5 mL)
3. 3
   洗浄The cartridge was eluted with methanol
4. 4
   その他to remove non-basic impurities
5. 5
   洗浄eluted with 3M NH3 in methanol
6. 6
   workup.ADDITIONFractions containing the title compound
7. 7
   濃縮concentrated under reduced pressure

実験手順

To a solution of benzyl [(1S)-1-benzyl-2-({(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl]carbamate (1.43 g, 3.14 mmol) from preparation 1 in dichloromethane (30 mL) and methanol (2 mL) was added TFA (20 ml) at 0° C. The reaction mixture was stirred for 5 hours and then concentrated under reduced pressure. The residue was dissolved in methanol (5 mL) and loaded onto a 20 g SCX2 cartridge (pre-wetted with methanol). The cartridge was eluted with methanol to remove non-basic impurities and then eluted with 3M NH3 in methanol. Fractions containing the title compound were combined and concentrated under reduced pressure to afford the title compound as a white solid in 90% yield, 1.01 g. 1H NMR (400 MHz, MeOH-d4) : 1.21 (d, 3H), 2.70 (dd, 1H), 2.78-2.84 (m, 1H), 3.17 (dd, 1H), 3.31-3.44 (m, 3H), 3.88-4.01 (m, 2H), 4.98 (s, 2H), 7.11-7.34 (m, 10H).

出典