Dicyclohexylcarbodiimide → Fmoc-asn(trt)-opfp

HRID 1110196

反応式

HRID 1110196 の反応式
[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([OH:28])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:46][C:47]1[C:52](O)=[C:51]([F:54])[C:50]([F:55])=[C:49]([F:56])[C:48]=1[F:57].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[NH:1]([C:29]([O:31][CH2:32][CH:33]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:30])[C@H:2]([C:26]([O:28][C:52]1[C:47]([F:46])=[C:48]([F:57])[C:49]([F:56])=[C:50]([F:55])[C:51]=1[F:54])=[O:27])[CH2:3][C:4](=[O:25])[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 640248Fmoc-Asn(Trt)-OH

生成物 1

HCID 15138257Fmoc-asn(trt)-opfp

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.5 g (2.51 mmol) of Fmoc-Asn(Trt)-OH are dissolved in 15 ml of tetrahydrofuran. 0.51 g (2.76 mmol) of pentafluoro-phenol is added, the solution is cooled to 0° and then 0.57 g (2.76 mmol) of dicyclohexyl-carbodiimide is also added in solid form. It is stirred at 0° for 30 minutes, at room temperature for 2 hours and again at 0° for 30 minutes. The dicyclohexylurea which has crystallized out is filtered off, and the filtrate is evaporated to dryness and triturated with 40 ml of diisopropyl ether. The powdery residue is filtered off, dried and recrystallized from methylene chloride/petroleum ether. Fmoc-Asn(Trt)-OPfp is obtained; m.p. 154°-156°, [α]D20 =-7.8° (THF).

後処理

  1. temperaturethe solution is cooled to 0°
  2. customThe dicyclohexylurea which has crystallized out
  3. filtrationis filtered off
  4. customthe filtrate is evaporated to dryness
  5. customtriturated with 40 ml of diisopropyl ether
  6. filtrationThe powdery residue is filtered off
  7. customdried
  8. customrecrystallized from methylene chloride/petroleum ether

出典と根拠

ORDレコード
ord-81158b16d707489b8214ac7ac824e4a5
出典データセット
uspto-grants-1994_06
特許番号
US05324833

関連ノート

読み込み中…