3,5-Dihydroxybenzoic Acid → 3,5-Dihydroxybenzamide

HRID 1372190

반응식

HRID 1372190 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5](O)=[O:6].Cl.C[N:14](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CCN(CC)CC>C(Cl)Cl.CCOC(C)=O.CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([NH2:14])=[O:6]

참가 물질

8

반응물 4

HCID 74243,5-Dihydroxybenzoic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 766043,5-Dihydroxybenzamide

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

After reaction step (a), the resulting amine (1 equiv.), 3,5-dihydroxybenzoic acid (1 equiv.), EDCI (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) (1.2 equiv.), HOBt (1-hydroxybenzotriazole hydrate) (1.2 equiv.), and Et3N (4 equiv.) in CH2Cl2.DMF (9:1) were stirred for 12 hours at room temperature. Then the reaction mixture was diluted with EtOAc and the organic layer washed with brine. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. Purification of the resulting crude product by flash silica gel chromatography provided corresponding 3,5-dihydroxybenzamide derivative. The above derivative (1 equiv.) and active carbonate 4 (1.1 equiv.) in THF were stirred under hydrogen atmosphere in presence of Pd—C (10%) for 12 hours at room temperature. Then the reaction mixture was filtered and the organic layer washed with brine. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. Purification of the resulting crude product by flash silica gel chromatography provided compound 134 as a solid.

후처리

  1. customAfter reaction step (a)
  2. washthe organic layer washed with brine
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customPurification of the resulting crude product by flash silica gel chromatography

출처 및 근거

ORD 기록
ord-c781951f050045288ea58b6dbd9a58ca
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157489B2

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