Diisopropylethylamine → ethyl 5-[4-[[N-[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]-N-[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propyl]amino]methyl]-3,5-dimethoxyphenoxy]valerate

HRID 362128

反応式

HRID 362128 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24](O)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2N=CC=CC=2N=N1.[F:60][C:61]([F:92])([F:91])[CH2:62][CH:63]([NH:69][CH2:70][C:71]1[C:86]([O:87][CH3:88])=[CH:85][C:74]([O:75][CH2:76][CH2:77][CH2:78][CH2:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])=[CH:73][C:72]=1[O:89][CH3:90])[CH:64]([O:67][CH3:68])[O:65][CH3:66].C(N(C(C)C)CC)(C)C>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:24]([N:69]([CH2:70][C:71]3[C:72]([O:89][CH3:90])=[CH:73][C:74]([O:75][CH2:76][CH2:77][CH2:78][CH2:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])=[CH:85][C:86]=3[O:87][CH3:88])[CH:63]([CH:64]([O:65][CH3:66])[O:67][CH3:68])[CH2:62][C:61]([F:91])([F:92])[F:60])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 1549133Fmoc-leucineHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphateHCID 22619160ethyl 5-[4-[[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propylamino]methyl]-3,5-dimethoxyphenoxy]valerate

生成物 1

HCID 22942077ethyl 5-[4-[[N-[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]-N-[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propyl]amino]methyl]-3,5-dimethoxyphenoxy]valerate収率 79.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 6.6 g (18.7 mmol) of N-[(9-fluorenyl)-methoxycarbonyl]-L-leucine and 9.7 g (18.7 mmol) of 7-azabenzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate in 50 ml of anhydrous dichloromethane was stirred at room temperature for 15 minutes. To this mixture were then added 6.0 g (12.4 mmol) of ethyl 5-[4-[[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propylamino]methyl]-3,5-dimethoxyphenoxy]valerate and 4.3 ml of (24.8 mmol) diisopropylethylamine. After stirring overnight at 250C the mixture was diluted with dichloromethane and washed in sequence with water, 10% citric acid solution, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over anhydrous magnesium sulphate andfiltered. The solvent was removed by evaporation and the residue was chromatographed on silica gel using 30% ethyl acetate in hexane for the elution. There were obtained 8.06 g of ethyl 5-[4-[[N-[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]-N-[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propyl]amino]methyl]-3,5-dimethoxyphenoxy]valerate; MS: m/e 839.4 [M+Na], 855.3 [M+K].

後処理

  1. washwashed in sequence with water, 10% citric acid solution, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customThe solvent was removed by evaporation
  4. customthe residue was chromatographed on silica gel using 30% ethyl acetate in hexane for the elution

出典と根拠

ORDレコード
ord-8439c3e448cb43f5a49be84f56c3ea70
出典データセット
uspto-grants-1999_02
特許番号
US05866684

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