Chlorotrimethylsilane → HCID 178474807、化合物

HRID 1106112

反応式

HRID 1106112 の反応式
[C:1]([NH:4][CH2:5][CH2:6][C:7](O)=[O:8])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:37]=[C:36]([OH:38])[C:35]([C:39]([OH:41])=[O:40])=[CH:34][N:33]=2)=[CH:28][CH:27]=1.C(N(CC)CC)C.C[Si](Cl)(C)C>ClCCl.C(#N)C>[C:1]([NH:4][CH2:5][CH2:6][C:7]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:37]=[C:36]([OH:38])[C:35]([C:39]([OH:41])=[O:40])=[CH:34][N:33]=2)=[CH:30][CH:31]=1)=[O:8])(=[O:3])[CH3:2]

参加物

9

反応物 6

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 76406N-Acetyl-beta-alanineHCID 178507442HCID 178507442、化合物

生成物 1

HCID 178474807HCID 178474807、化合物収率 96.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

A solution of 4.6 g (35 mmol) of N-acetyl-beta-alanine, 100 ml acetonitrile, and 3.9 ml (35 mmol) of N-methylmorpholine is stirred at -15° C. and 5.0 ml (38.5 mmol) of isobutyl chloroformate is added. After 30 minutes at -15° C. a solution prepared from 4.05 g (17.5 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.35 ml (52.5 mmol) of triethylamine, and 7.96 ml (62.7 mmol) of trimethylsilyl chloride in 100 ml of dichloromethane is added and the mixture stirred at -10° C. for 1 hour and at room temperature overnight. The mixture is evaporated to near dryness in vacuo and treated with 200 ml of water. The product is precipitated by acidifying to pH 2.0 and is filtered, washed with water, isopropanol, ether, and dried to give 5.8 g of 2-[4-(N-acetyl-beta-alanylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid.

後処理

  1. additionis added
  2. customThe mixture is evaporated
  3. additiontreated with 200 ml of water
  4. customThe product is precipitated
  5. filtrationis filtered
  6. washwashed with water, isopropanol, ether
  7. customdried

出典と根拠

ORDレコード
ord-2899a12b1d5040b5941ba4b0bcb1bad2
出典データセット
uspto-grants-1982_01
特許番号
US04311699

関連ノート

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