N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine → Fmoc-L-cysteine

HRID 1243281

反応式

HRID 1243281 の反応式
[C:1]([NH:18][C@H:19]([C:41]([OH:43])=[O:42])[CH2:20][S:21]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([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]>C(Cl)Cl>[C:1]([NH:18][C@H:19]([C:41]([OH:43])=[O:42])[CH2:20][SH:21])([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

3

反応物 1

HCID 128239N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine

生成物 1

HCID 11024349Fmoc-L-cysteine収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of Fmoc-S-trityl-L-cysteine (10.0 g, 17.1 mmol), in DCM containing 15% trifluoroacetic acid (TFA) and 5% TES (total volume 150 mL) was stirred at room temperature. After 10 min the reaction was evaporated to dryness, the solid residue was washed three times with 150 mL n-pentane and then dried under high vacuum. 4.46 g of Fmoc-L-cysteine was obtained as a colorless solid. This material was dissolved in DCM (20 mL) containing 7% TFA. 1.0 g Trityl chloride resin (Novabiochem, loading 2.05 mmol of active chlorine) was added in one portion. The solution was slowly agitated overnight (orbital shaker, or slow stirring on a magnetic stirrer). The resin was isolated on a sintered glass funnel, washed with DCM (5×40 mL), methanol (1×40 mL) and again with DCM and dried overnight in vacuo.

後処理

  1. customAfter 10 min the reaction was evaporated to dryness
  2. washthe solid residue was washed three times with 150 mL n-pentane
  3. customdried under high vacuum

出典と根拠

ORDレコード
ord-042c8c9670cb4cb690341602466a45b4
出典データセット
uspto-grants-2006_10
特許番号
US07119073B2

関連ノート

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