Tributylphosphine → 3-{4-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yl)-3-methyl-butoxy]-benzoylamino}-propionic acid methyl ester

HRID 1669315ノート

反応式

HRID 1669315 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH3:56][O:57][C:58](=[O:71])[CH2:59][CH2:60][NH:61][C:62](=[O:70])[C:63]1[CH:68]=[CH:67][C:66](O)=[CH:65][CH:64]=1>C1(C)C=CC=CC=1>[CH3:56][O:57][C:58](=[O:71])[CH2:59][CH2:60][NH:61][C:62](=[O:70])[C:63]1[CH:68]=[CH:67][C:66]([O:13][CH:8]([C:6]2[CH:5]=[C:4]([CH3:14])[C:3]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=3)=[C:2]([CH3:1])[CH:7]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:65][CH:64]=1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 597293931-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yl)-3-methyl-butan-1-ol

生成物 1

HCID 673433583-{4-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yl)-3-methyl-butoxy]-benzoylamino}-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yl)-3-methyl-butan-1-ol (270 mg, 0.8 mmol) in toluene (8 mL) is added 1,1′-(azodicarbonyl) dipiperidine (ADDP, 304 mg, 1.21 mmol) at 0° C., followed by the addition of tributylphosphine (0.3 mL, 12.1 mmol) and 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (215 mg, 0.96 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving 3-{4-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yl)-3-methyl-butoxy]-benzoylamino}-propionic acid methyl ester. The ester product is taken into methanol (2 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 5 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1.1 mL), extracted with ethyl acetate. The organic layers are dried and concentrated to afford 51 mg of the titled compound. MS (ES): 528.3 [M+H]+.

後処理

  1. washeluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate

出典と根拠

ORDレコード
ord-c4e309e9e4d44175acf2708f1cbde33b
出典データセット
uspto-grants-2011_08
特許番号
US07989457B2

反応ノート

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