Diisopropylethylamine → N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycyl-S-trityl-L-cysteinamide

HRID 630663ノート

反応式

HRID 630663 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:23]([S:42][CH2:43][C@@H:44]([C:46]([NH:48]CC(N)=O)=[O:47])[NH2:45])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][C:20]([NH:45][C@H:44]([C:46]([NH2:48])=[O:47])[CH2:43][S:42][C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 93124Fmoc-Gly-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89544895S-Trityl-L-cysteinylglycinamide

生成物 1

HCID 89544531N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycyl-S-trityl-L-cysteinamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

1.00 g (3.36 mmol) of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycine was dissolved in 30 ml dichloromethane. 1.41 g (3.36 mmol) S-Trityl-L-cysteinylglycinamide, 0.59 ml (3.36 mmol) N,N-diisopropylethylamine and 1.28 g (3.36 mmol) HATU were added. The reaction mixture was heated for 30 min in a sealed tube at 60° C. in a microwave synthesizer. From the reaction mixture the solvent was removed under reduced pressure. The raw product was dissolved in dichloromethane and chromatographed over approx. 300 ml silica gel. Solvents used were dichloromethane, dichloromethane/methanol 20/1, dichloromethane/methanol 10/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. This gave 1.63 g (2.06 mmol, 81% of theory) of the desired product.

後処理

  1. customFrom the reaction mixture the solvent was removed under reduced pressure
  2. dissolutionThe raw product was dissolved in dichloromethane
  3. customchromatographed over approx. 300 ml silica gel
  4. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-1e4e5f3fb09840acbac4ca8de9857b30
出典データセット
uspto-grants-2016_04
特許番号
US09315543B2

反応ノート

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