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Diisopropyl Ether → N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-(triphenylmethyl)-L-glutamine 2,3,4,5,6-pentafluorophenyl ester

HRID 1110197
ノート
印刷プレビュー

反応式

HRID 1110197 の反応式
[NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OC(C)C)(C)C.[F:54][C:55]1[C:60](O)=[C:59]([F:62])[C:58]([F:63])=[C:57]([F:64])[C:56]=1[F:65].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([O:29][C:60]1[C:55]([F:54])=[C:56]([F:65])[C:57]([F:64])=[C:58]([F:63])[C:59]=1[F:62])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7914Diisopropyl EtherHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 10919157(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-[(triphenylmethyl)carbamoyl]butanoic acid

生成物 1

HCID 11297250N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-(triphenylmethyl)-L-glutamine 2,3,4,5,6-pentafluorophenyl ester

試薬・触媒・溶媒

1
HCID 8857Ethyl Acetate溶媒

実験手順

1.5 g (2.27 mmol) of Fmoc-Gln(Trt)-OH×0.5 diisopropyl ether and 0.46 g (2.5 mmol) of pentafluoro-phenol are dissolved in 35 ml of ethyl acetate, cooled to 0° and, while stirring, 0.52 g (2.5 mmol) of dicyclohexylcarbodiimide is added. The mixture is stirred at 0° for 1 hour and at room temperature for 3 hours, and insoluble material is filtered off and washed with tetrahydrofuran. The filtrate is evaporated to dryness, and the residue is dissolved in 30 ml of tetrahydrofuran. Slow addition of petroleum ether while stirring results in crystallization of Fmoc-Gln(Trt)-OPfp; m.p. 185°-187°, [α]D20 =-16.4° (THF).

後処理

  1. temperaturecooled to 0°
  2. stirringThe mixture is stirred at 0° for 1 hour and at room temperature for 3 hours
  3. filtrationinsoluble material is filtered off
  4. washwashed with tetrahydrofuran
  5. customThe filtrate is evaporated to dryness
  6. dissolutionthe residue is dissolved in 30 ml of tetrahydrofuran
  7. additionaddition of petroleum ether
  8. stirringwhile stirring

出典と根拠

ORDレコード
ord-b4cbe7779ee6426e84775aaa1ac41808
出典データセット
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05324833

反応ノート

読み込み中…

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