4-Methylmorpholine → HCID 178475081、化合物

HRID 1106120ノート

反応式

HRID 1106120 の反応式
[C:1]([NH:4][C@@H:5]([C:9]([OH:11])=O)[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:39]=[C:38]([OH:40])[C:37]([C:41]([OH:43])=[O:42])=[CH:36][N:35]=2)=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C)C(=O)C.ClCCl>[C:1]([NH:4][C@@H:5]([C:9]([NH:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[N:39]=[C:38]([OH:40])[C:37]([C:41]([OH:43])=[O:42])=[CH:36][N:35]=2)=[CH:32][CH:33]=1)=[O:11])[CH:6]([CH3:7])[CH3:8])(=[O:3])[CH3:2]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 76475N-acetyl-D-valineHCID 178507442HCID 178507442、化合物

生成物 1

HCID 178475081HCID 178475081、化合物収率 49.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A suspension of 11.41 g (71.7 mmol) of N-acetyl-D-valine and 150 ml of dichloromethane is stirred at room temperature and 7.9 ml (71.7 mmol) of N-methylmorpholine is added. The resulting solution is cooled to -10° C. and 9.3 ml (71.7 mmol) of isobutyl chloroformate is added. The reaction mixture is stirred at -15°±5° C. for 45 min and an ice cold solution of 11.09 g (48 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.4 ml (52.8 mmol) of triethylamine, and 200 ml of N,N-dimethylacetamide is added while keeping the temperature below -10° C. The mixture is stirred at 0°-5° C. for 2 hrs and overnight at room temperature. A small amount of solid is filtered and the filtrate is evaporated to dryness. Water is added to the residue and the resulting solid filtered, washed with water, ethyl acetate, and ether and dried to give 8.9 g of 2-[4-(N-acetyl-D-valylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. A second crop, obtained from the aqueous filtrate, weighs 2.35 g. [α]D23 +4.50 (cl, pH 7).

後処理

  1. temperatureThe resulting solution is cooled to -10° C.
  2. stirringThe reaction mixture is stirred at -15°±5° C. for 45 min
  3. customthe temperature below -10° C
  4. stirringThe mixture is stirred at 0°-5° C. for 2 hrs and overnight at room temperature
  5. filtrationA small amount of solid is filtered
  6. customthe filtrate is evaporated to dryness
  7. additionWater is added to the residue
  8. filtrationthe resulting solid filtered
  9. washwashed with water, ethyl acetate, and ether
  10. customdried

出典と根拠

ORDレコード
ord-e9b9f4b2eb5a45d9985549e91d7b8bdb
出典データセット
uspto-grants-1982_01
特許番号
US04311699

反応ノート

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