Реакция #1569092

Уравнение реакции

(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

HATU

DIPEA

(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine

→

title compound

(2S,4S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1yl)carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Другоеthe cooling bath removed
3. 3
   workup.ADDITIONAfter 4 h the mixture was diluted with ethyl acetate
4. 4
   Промывкаwashed with water
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated

Методика

To a solution of (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (Aldrich) (7.5 g, 16.593 mmol) in DMF (100 mL) were added HATU (6.93 g, 18.252 mmol) and DIPEA (14.36 mL, 82.965 mmol) and the mixture was cooled to 0° C. (R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine (2.44 g, 16.593 mmol) was added dropwise and the cooling bath removed. After 4 h the mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated to afford the title compound as an off white solid (9.6 g) which was used without purification. LC-MS: 582 (M+H).

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