Potassium Carbonate → (3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

HRID 1159595

반응식

HRID 1159595 반응식
[CH3:1][C:2]1([CH3:15])[O:11][C:10]2[C:5](=[CH:6][C:7]([C:12]#[N:13])=[CH:8][CH:9]=2)[C@@H:4]2[O:14][C@H:3]12.[NH:16]1[CH:20]=[CH:19][NH:18][C:17]1=[S:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:14][C@@H:3]1[C@H:4]([S:21][CH:17]2[N:18]=[CH:19][CH:20]=[N:16]2)[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[CH:6]=2)[O:11][C:2]1([CH3:15])[CH3:1]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 12013862-MercaptoimidazoleHCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

생성물 1

HCID 68644174(3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S,S)-2,2-Dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene-6-carbonitrile (1 mmoL), 1,3-dihydro-imidazole-2-thione (1 mmoL) and anhydrous K2CO3 (1.5 mmoL) in DMF (5 mL) were heated at 100° C. for 4˜6 hrs. The solid was filtered off and the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated NH4Cl, brine, then dried over anhydrous Na2SO4, filtered and concentrated to yield a yellow oil. Silica gel chromatography separation yielded the title compound as a white solid.

후처리

  1. filtrationThe solid was filtered off
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated NH4Cl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow oil
  8. customSilica gel chromatography separation

출처 및 근거

ORD 기록
ord-9305f411534b41ee978505cf1fe25b0b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812183B2

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