4-Methylmorpholine → HCID 178474779、化合物

HRID 2286621ノート

反応式

HRID 2286621 の反応式
[C:1]([NH:4][C@H:5]([C:11]([OH:13])=O)[CH2:6][CH2:7][C:8](=[O:10])[NH2:9])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:41]=[C:40]([OH:42])[C:39]([C:43]([OH:45])=[O:44])=[CH:38][N:37]=2)=[CH:32][CH:31]=1.CN1CCOCC1>CN(C)C=O>[C:1]([NH:4][CH:5]([C:11]([NH:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[N:41]=[C:40]([OH:42])[C:39]([C:43]([OH:45])=[O:44])=[CH:38][N:37]=2)=[CH:34][CH:35]=1)=[O:13])[CH2:6][CH2:7][C:8](=[O:10])[NH2:9])(=[O:3])[CH3:2]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 182230AceglutamideHCID 178507442HCID 178507442、化合物

生成物 1

HCID 178474779HCID 178474779、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of 14.1 g (75mmol) of N-acetyl-L-glutamine and 9.75 ml (75 mmol) of triethylamine in 150 ml of dimethylformamide is stirred at -15° to -20° C. and 9.75 ml (75 mmol) of isobutyl chloroformate is added. After stirring at -15° to -20° C. for 30 min a cold solution of 11.6 g (50 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 7.15 ml (50 mmol) of N-methylmorpholine in 200 ml of dimethylformamide is added at -15° C. The reaction mixture is stirred at -15° C. for 20 min at 5° C. for 3 hrs, and at room temperature overnight. The reaction mixture is evaporated and the residue treated with water. The pH is lowered to 2.5 with hydrochloric acid and the solid is filtered, washed with water, and dried to afford 17.3 g of 2-[4-(N-acetyl-DL-glutaminylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 247°-248° C. dec. [α]D25 -2.8 (c0.7, DMSO).

後処理

  1. additionis added at -15° C
  2. customat room temperature
  3. customovernight
  4. customThe reaction mixture is evaporated
  5. additionthe residue treated with water
  6. filtrationthe solid is filtered
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-e0ec169cc2994278b4ffcf9e68010d7f
出典データセット
uspto-grants-1981_05
特許番号
US04267180

反応ノート

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