Potassium Carbonate → N-(tert-butoxycarbonyl)-4-(2-thienyl)-L-phenylalanine methyl ester

HRID 24628

反応式

HRID 24628 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17](=[O:42])[C@H:18]([CH2:27][C:28]1[CH:33]=[CH:32][C:31](OS(C(F)(F)F)(=O)=O)=[CH:30][CH:29]=1)[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>C1(C)C=CC=CC=1.CN(C=O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:16][C:17](=[O:42])[C@H:18]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:32][CH:33]=1)[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27339602-Thiopheneboronic acidHCID 10455198(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

生成物 1

HCID 10309111N-(tert-butoxycarbonyl)-4-(2-thienyl)-L-phenylalanine methyl ester収率 62.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 21735183Dimethylformamide toluene溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 2-thienylboronic acid (1.135 g) and anhydrous K2CO3 (2.23 g) in toluene/DMF (75 mL/7.5 mL) under N2 was added a solution of N-(tert-butoxycarbonyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (3.42 g) in 5 mL of toluene. Pd(PPh3)4 (1.4 g) was added and the mixture was heated at 80° C. for 24 h. After usual work-up as shown in Example 1 the crude material was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3) to yield N-(tert-butoxycarbonyl)-4-(2-thienyl)-L-phenylalanine methyl ester (1.81 g). ESMS: m/z 362 (MH+).

後処理

  1. customwas purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3)

出典と根拠

ORDレコード
ord-1db0bfad9af543919c7b8344aca7a271
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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