Chlorotrimethylsilane → HCID 178474807, 화합물

HRID 2286617

반응식

HRID 2286617 반응식
[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]

참가 물질

9

반응물 6

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 76406N-Acetyl-beta-alanineHCID 178507442HCID 178507442, 화합물

생성물 1

HCID 178474807HCID 178474807, 화합물수율 96.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f037f40299e640d1a1ebcb2e47177c77
출처 데이터셋
uspto-grants-1981_05
특허 번호
US04267180

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