反応 #590803

反応方程式

benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate

Fmoc-glycine

1H-benzo[d][1,2,3]triazol-1-ol

(S)-methyl-4,4-difluoropyrrolidine-2-carboxylate TFA salt

→

(R)-methyl 1-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)acetyl)-4,4-difluoropyrrolidine-2-carboxylate

溶媒

DMF

DCM

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at RT
2. 2
   洗浄washed with water
3. 3
   その他The organic layer was dried
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The crude oil was purified by silica gel chromatography, 0-5% MeOH/DCM

実験手順

A round bottom flask was charged with Fmoc-glycine (756 mg, 2543 μmol), 1H-benzo[d][1,2,3]triazol-1-ol (412 mg, 3052 μmol), (S)-methyl-4,4-difluoropyrrolidine-2-carboxylate TFA salt (710 mg, 2543 μmol), Hunig'sBase (2221 μl, 12717 μmol) and 10.2 mL DMF. The mixture was stirred for 5 min at RT, and benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (1350 mg, 3052 μmol) was added. The reaction mixture was stirred overnight at RT. The solution was diluted with DCM and washed with water. The organic layer was dried, filtered, and concentrated. The crude oil was purified by silica gel chromatography, 0-5% MeOH/DCM to provide (R)-methyl 1-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)acetyl)-4,4-difluoropyrrolidine-2-carboxylate. MS: [M+H]=445.

出典