反応 #4860

反応方程式

3-phenylpropylamine

CH2Cl2

title compound

N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-D-alanine

NMM

→

title product

N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

溶媒

EtOAc

反応条件

後処理

1. 1
   workup.ADDITIONTo this solution was added 5.7 g (43.6 mmole) of IBCF
2. 2
   温度the mixture warmed to 10° C
3. 3
   温度The solution was then cooled to -25° C.
4. 4
   その他the reaction
5. 5
   温度to warm to room temperature
6. 6
   抽出extracted with three 100 ml portions of 0.5N KHSO4
7. 7
   抽出The combined aqueous washes were extracted with 100 ml of EtOAc
8. 8
   洗浄The combined organic was then washed with one 150 ml portion of brine
9. 9
   乾燥before drying it over Na2SO4
10. 10
    その他All solvent was removed under reduced pressure

実験手順

A CH2Cl2 solution (100 ml) of the title compound from Example 9, (16.6 g, 43.6 mmole) was charged with 4.4 g (43.6 mmoles) of NMM and cooled to -45° C. To this solution was added 5.7 g (43.6 mmole) of IBCF and the mixture warmed to 10° C. The solution was then cooled to -25° C. before adding 7.4 g (54.5 mmole) of 3-phenylpropylamine. After allowing the reaction to warm to room temperature and stand overnight, it was diluted with 300 ml of EtOAc and extracted with three 100 ml portions of 0.5N KHSO4. The combined aqueous washes were extracted with 100 ml of EtOAc and this extract was combined with the original organic phase. The combined organic was then washed with one 150 ml portion of brine before drying it over Na2SO4. All solvent was removed under reduced pressure to give the title product as a foam. This material was chromatographed to give 10 g (46%) of a compound identical to diastereomer S of Example 3.

出典