Pyridine → n-Fmoc-o-t-butyl-l-serinyl fluoride

HRID 7234

反応式

HRID 7234 の反応式
[C:1]([NH:18][C@H:19]([C:26]([OH:28])=O)[CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:37]>ClCCl>[C:1]([NH:18][C@H:19]([C:26]([F:37])=[O:28])[CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

参加物

5

反応物 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserine

生成物 1

HCID 11315144n-Fmoc-o-t-butyl-l-serinyl fluoride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-FMOC-O-t-Butyl-L-serine (10 g, 26.07 mmol) (Bachem) was dissolved in dichloromethane (135 mL). Pyridine (2.11 mL, 26.07 mmol) (Aldrich) and cyanuric fluoride (3.52 g, 26.07 mmol) (Aldrich) were successively added at room temperature and the mixture was stirred overnight. Ice cold water (100 mL) was added and the resulting slurry was filtered. The filtrate was poured into a separatory funnel and the layers were separated. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford N-FMOC-O-t-butyl-L-serinyl fluoride as a colorless oil which solidified upon standing. (Yield 9.79 g., 97%).

後処理

  1. filtrationthe resulting slurry was filtered
  2. additionThe filtrate was poured into a separatory funnel
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7e467cb3ee834f5c8c6a348a4e446e43
出典データセット
uspto-grants-2006_08
特許番号
US07084270B2

関連ノート

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