4-Methylmorpholine → HCID 178474779, 화합물

HRID 1106116노트

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HRID 1106116 반응식
[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.C(OC(Cl)=O)C(C)C.[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]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 182230AceglutamideHCID 178507442HCID 178507442, 화합물

생성물 1

HCID 178474779HCID 178474779, 화합물수율 86.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
5 °C

실험 절차

A solution of 14.1 g (75 mmol) 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 isobutylchloroformate 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 mml) of N-methylmorpholine in 200 ml of dimethylformamide is added at -15° C. The reaction mixture is stirred at -15° 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]23D -2.8° (c0.7, DMSO)

후처리

  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

출처 및 근거

ORD 기록
ord-3582722e0c73412ca77c0a1d2352e0ac
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04311699

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