N-(9-Fluorenylmethoxycarbonyloxy)succinimide → Fmoc-Pro(4-OH)-OMe

HRID 2069877

反応式

HRID 2069877 の反応式
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.[C:12](ON1C(=O)CCC1=O)([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13]>C(=O)([O-])[O-].[Na+].[Na+].C1COCC1>[N:6]1([C:12]([O:14][CH2:15][CH:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[C:28]2=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:13])[CH2:7][CH:8]([OH:10])[CH2:9][C@H:5]1[C:4]([O:3][CH3:2])=[O:11]

参加物

4

反応物 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

生成物 1

HCID 68974574Fmoc-Pro(4-OH)-OMe

試薬・触媒・溶媒 1

HCID 70538864sodium carbonate THF溶媒

実験手順

L-hydroxyproline methylester hydrochloride is reacted with Fmoc-OSu in aqueous 1.0 N sodium carbonate/THF at room temperature. After completion of the reaction, Fmoc-Pro(4-OH)—OMe is isolated by precipitation. Fmoc-Pro(4-OH)—OMe is then added dropwise into a solution of trisphosgene (0.6 eq.) in THF to give a chlorocarbonate intermediate. After 1 h dimethylaminopyridine (1.0 eq.) and N-Boc-diaminoethane (6.0 eq.) are added and the reaction is stirred at room temperature. After completion of the reaction, the solvent is removed in vacuo and the resulting Fmoc-Pro(4-OCO—NH—CH2—CH2—NH-Boc)-OMe is extracted from a two phase system of ethyl acetate/0.1 M HCl to give crude product (MH+=554) which is purified by crystallization from ethyl acetate. The methyl ester is then cleaved to the free acid by treatment with 1N NaOH in dioxane/water and the product Fmoc-Pro(4-OCO—NH—CH2—CH2—NH-Boc)-OH is purified on silica gel, [(M+Na)]+=562).

後処理

  1. customAfter completion of the reaction

出典と根拠

ORDレコード
ord-3d290819a6ba45d78e33e281d3e1a4dc
出典データセット
uspto-grants-2012_10
特許番号
US08299209B2

関連ノート

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