Isopropanol → 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran

HRID 1460834

반응식

HRID 1460834 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH2:15])[C:7]=2[CH:16]=1)#[N:2].ClC/[C:19](/[O:25][CH3:26])=[CH:20]\[C:21](OC)=O.[C:27](=[O:30])([O-])[O-].[K+].[K+].[I-].[Na+].[CH:35]([OH:38])(C)C>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH:15]/[CH:21]=[C:20](/[O:30][CH3:27])\[CH2:19][O:25][CH:26]=[C:35]=[O:38])[C:7]=2[CH:16]=1)#[N:2]

참가 물질

6

반응물 5

HCID 3776IsopropanolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 6364655Methyl (E)-4-Chloro-3-methoxy-2-butenoateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

생성물 1

HCID 867446436-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran

실험 절차

A mixture of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-amino-2H-1-benzopyran (4.7 g), 4-chloro-3-methoxy-2-E-butenoic acid, methyl ester (3.55 g), potassium carbonate (5.95 g) and sodium iodide (3.2 g) was refluxed for 3 hours in isopropanol. After cooling the mixture was filtered and solvent removed from the filtrate under reduced pressure, to give 1.1 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran, a compound of formula (6). The compound was used in the next reaction (Example 3) with no further purification.

후처리

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. customsolvent removed from the filtrate under reduced pressure

출처 및 근거

ORD 기록
ord-b625efb7d2a8409a8eaffb5048c2787c
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05072006

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