Phthalic Anhydride → (2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid

HRID 622792

反応式

HRID 622792 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C1(C)C=CC=CC=1>[CH2:7]([O:8][C:9]([CH2:11][CH2:12][C@H:13]([N:17]1[C:21](=[O:22])[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=[O:23])[C:14]([OH:16])=[O:15])=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

参加物

4

反応物 2

HCID 6811Phthalic AnhydrideHCID 122337L-Glutamic acid, 5-(phenylmethyl) ester

生成物 1

HCID 11100670(2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid収率 60.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

16 g of L-glutamic acid γ-benzyl ester and 11 g of phthalic anhydride, both finely powdered, were stirred in 20 ml of toluene at reflux temperature for 2 hours. 50 ml of toluene were added and the mixture was evaporated. A further 80 ml of toluene were then added and the mixture was left to crystallize. Recrystallization from toluene yielded 15 g of α(S)-(2-benzyloxycarbonylethyl)-1,3-dihydro-1,3-dioxo-2-isoindoleacetic acid of melting point 96°-98° C.; [α]D20 =-50.4° (c=1 in methanol).

後処理

  1. temperatureat reflux temperature for 2 hours
  2. customthe mixture was evaporated
  3. additionA further 80 ml of toluene were then added
  4. waitthe mixture was left
  5. customto crystallize
  6. customRecrystallization from toluene

出典と根拠

ORDレコード
ord-53de2e23dd3245e084f4c8875811a97d
出典データセット
uspto-grants-1988_09
特許番号
US04772701

関連ノート

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