Toluene → 4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester

HRID 1429125ノート

反応式

HRID 1429125 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[NH:18][CH2:17][CH:16]([O:19][C:20](=[O:30])[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH2:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:31]([O-:34])(O)=O.[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH2:47]([NH:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=1)[CH2:48][CH2:49][CH2:50][CH:51]=[CH:52][CH3:53]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[N:18]([C:31](=[O:34])[N:54]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH:52]=[CH2:53])[CH2:55][C:56]3[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=3)[CH2:17][CH:16]([O:19][C:20](=[O:30])[C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[CH2:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

参加物

7

反応物 5

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium Bicarbonate2 回HCID 668708334-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl esterHCID 66871144Hept-5-enyl-(p-methoxybenzyl)-amine

生成物 1

HCID 668705064-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of compound 1c (4.5 g, 10.8 mmol) in THF (160 mL) was added NaHCO3 (1 tablespoon) and phosgene in toluene (1.93 M, 11.5 mL, 22 mmol). The mixture was vigorously stirred for 1 h at room temperature, and then filtered and evaporated. The residue was dissolved in CH2Cl2 (160 mL), and NaHCO3 (1 tablespoon) and hept-5-enyl-(p-methoxybenzyl)-amine (4.3 g, 18.5 mmol) were added. After stirring overnight at room temperature the reaction mixture was filtered and evaporated to dryness. Flash column chromatography on silica gel (EtOAc:toluene 25:75→40:60) gave the title compound (6.59 g, 90%) as a light brown syrup.

後処理

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe residue was dissolved in CH2Cl2 (160 mL)
  4. stirringAfter stirring overnight at room temperature the reaction mixture
  5. filtrationwas filtered
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-573144564fb6417389bb13af46c45d25
出典データセット
uspto-grants-2015_01
特許番号
US08937080B2

反応ノート

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