Hydrochloric Acid → [2-Cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetic acid

HRID 412399노트

반응식

HRID 412399 반응식
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=3[CH:25]=2)=[CH:11][CH:10]=[C:9]1[C:26]#[N:27])(C)(C)C.[OH-].[Na+].Cl>C(O)C>[C:26]([C:9]1[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=3[CH:25]=2)=[CH:11][CH:10]=1)#[N:27]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12044964tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate

생성물 1

HCID 12044965[2-Cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate (2.2 g, 5.8 mmol), and sodium hydroxide (1.6 g, 40 mmol) in ethanol (200 ml) was heated to reflux for 2 hours. After cooling to room temperature the mixture was acidified with diluted hydrochloric acid, and extracted with ethylacetate. The ethylacetate solution was dried over magnesium sulfate, filtered, and concentrated in vacuo. Recrystallization from ethylacetate/hexane afforded the title compound, m.p. 207-209° C. (1.2 g, 64%); 1H-NMR (DMSO-d6) δ 1.61 (s, 6H), 4.77 (s, 2H), 6.35 (d, J=4 Hz, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.09 (d, j=4.1 Hz, 1H), 7.26 (m, 2H), 10.43 (s, 1H), MS (APCI (−)) m/z 324 (M−H)−.

후처리

  1. temperatureto reflux for 2 hours
  2. extractionextracted with ethylacetate
  3. dry with materialThe ethylacetate solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethylacetate/hexane

출처 및 근거

ORD 기록
ord-fc3b920c49284984aa49e06a6e08cb01
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562857B2

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