Water → HCID 86756336、化合物

HRID 567944ノート

反応式

HRID 567944 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:22]([NH:24][CH2:25][C@@H:26]([C:56]([O:58]C(C)(C)C)=[O:57])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:49]([O:51]C(C)(C)C)=[O:50])[CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44]C(C)(C)C)=[CH:40][CH:39]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:23])[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.O>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:22]([NH:24][CH2:25][C@@H:26]([C:56]([OH:58])=[O:57])[CH2:27][C:28]1([C:33]([NH:35][C@H:36]([C:49]([OH:51])=[O:50])[CH2:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:23])[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86756335HCID 86756335、化合物

生成物 1

HCID 86756336HCID 86756336、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

Tert-butyl (S,S,S)-N-(1-[3-(N6-benzyloxycarbonyl-N2-mesyllysylamino)-2-(tert-butoxycarbonyl)propyl]-1-cyclopentylcarbonyl)-O4-tert-butyltyrosinate (404 g) was dissolved in dichloromethane (810 ml). Anisole (769 g) was added in one portion and then trifluoroacetic acid (1.158 kg) added dropwise over approximately 10 minutes. On completion of the addition, the reaction was stirred at 35° C. for 6 hours and then stirred at room temperature overnight. Water (1000 ml) was added and three layers formed. The top and bottom layers were combined, dissolved in ethyl acetate (2 l) and the resulting solution washed with brine. The organic phase was mixed with brine, the pH adjusted to 3 and the layers allowed to separate. Three layers formed. The organic phases were separated, taken up in ethyl acetate and extracted with saturated aqueous sodium bicarbonate (1.6 l) solution and brine (0.5 l). The combined aqueous layers were washed with ethyl acetate, then acidified and extracted with ethyl acetate to give an ethyl acetate solution (1.54 l) of the title compound. This solution was either used directly (e.g. see Example 1) or the solvent removed to provide the title compound.

後処理

  1. additionOn completion of the addition
  2. stirringstirred at room temperature overnight
  3. customthree layers formed
  4. washthe resulting solution washed with brine
  5. additionThe organic phase was mixed with brine
  6. customto separate
  7. customThree layers formed
  8. customThe organic phases were separated
  9. extractionextracted with saturated aqueous sodium bicarbonate (1.6 l) solution and brine (0.5 l)
  10. washThe combined aqueous layers were washed with ethyl acetate
  11. extractionextracted with ethyl acetate

出典と根拠

ORDレコード
ord-38332fbfa447458f9f59438fa36b02d4
出典データセット
uspto-grants-2001_01
特許番号
US06180665B2

反応ノート

読み込み中…