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

HRID 1243281

반응식

HRID 1243281 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

HCID 11024349Fmoc-L-cysteine수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-042c8c9670cb4cb690341602466a45b4
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119073B2

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