P-Toluic Acid → 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-

HRID 3669

反応式

HRID 3669 の反応式
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(N(CC)CC)C.[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>C(OCC)(=O)C.C(OC)(C)(C)C>[C:6]1(=[O:7])[N:2]([O:1][C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=2)=[O:23])[C:3](=[O:8])[CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 7470P-Toluic AcidHCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 80170N-Hydroxysuccinimide

生成物 1

HCID 64224042,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-収率 94%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

2.42 g (0.021 mol) of N-hydroxysuccinimide and 5.06 g (0.050 mol) of triethylamine were initially introduced into 5 ml of ethyl acetate and the suspension was stirred at room temperature. 2.72 g (0.020 mol) of solid 4-toluic acid were added to this suspension in the course of 5 min. and then a solution of 5.64 g (0.21 mol) of diphenyl chlorophosphate was added dropwise in the course of 20 min., the reaction mixture warming to about 35° C. The mixture was stirred at room temperature for 1 hour until the reaction was complete. The reaction mixture was then diluted with 100 ml of ethyl acetate and the organic phase was washed with 50 ml each of water, 2N hydrochloric acid and 10% strength aqueous sodium hydrogencarbonate solution and then evaporated. 4.65 g of crude product were isolated, which was then stirred at room temperature for 30 minutes with 20 ml of methyl tert-butyl ether. The white crystalline solid was filtered off and dried at 50° C. and 10 mbar. 4.28 g (94%) of 4-toluic acid succinimidyl ester were isolated.

後処理

  1. temperaturethe reaction mixture warming to about 35° C
  2. stirringThe mixture was stirred at room temperature for 1 hour until the reaction
  3. washthe organic phase was washed with 50 ml each of water, 2N hydrochloric acid and 10% strength aqueous sodium hydrogencarbonate solution
  4. customevaporated
  5. custom4.65 g of crude product were isolated
  6. filtrationThe white crystalline solid was filtered off
  7. customdried at 50° C.

出典と根拠

ORDレコード
ord-fa9e36ab9df044eca0ae8f17c3acb777
出典データセット
uspto-grants-1998_03
特許番号
US05734064

関連ノート

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