Pyridine → Benzoate

HRID 4989

반응식

HRID 4989 반응식
C(Cl)(Cl)=[O:2].[CH3:5][C@H:6]1[C@@H:37]([CH:38]([CH3:40])[CH3:39])[O:36][C:34](=[O:35])[C:33]2[N:29]([CH2:30][CH2:31][CH:32]=2)[C:27](=[O:28])[C:24]2=[CH:25][O:26][C:22](=[N:23]2)[CH2:21][C:19](=[O:20])[CH2:18][C@H:17]([OH:41])[CH:16]=[C:15]([CH3:42])[CH:14]=[CH:13][CH2:12][NH:11][C:9](=[O:10])[CH:8]=[CH:7]1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.CO>[CH3:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].[C:22]([O-:26])(=[O:2])[C:21]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH3:5][C@H:6]1[C@@H:37]([CH:38]([CH3:39])[CH3:40])[O:36][C:34](=[O:35])[C:33]2[N:29]([CH2:30][CH2:31][CH:32]=2)[C:27](=[O:28])[C:24]2=[CH:25][O:26][C:22](=[N:23]2)[CH2:21][C:19](=[O:20])[CH2:18][C@H:17]([OH:41])[CH:16]=[C:15]([CH3:42])[CH:14]=[CH:13][CH2:12][NH:11][C:9](=[O:10])[CH:8]=[CH:7]1

참가 물질

8

반응물 3

HCID 1049PyridineHCID 6371PhosgeneHCID 5459319Virginiamycin M1

생성물 3

HCID 242BenzoateHCID 7991Pentanoic AcidHCID 5459319Virginiamycin M1

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매

실험 절차

The n-propionate, n-valerate, n-phenylacetate and benzoate derivatives of Virginiamycin M1 were prepared using the respective carbonyl chlorides. The respective carbonyl chloride (1.0 mmole) was added to a stirring solution of virginiamycin M1 (0.50 g, 0.95 mmole), pyridine (84 μl) and 4-dimethylaminopyridine (20 μg) at room temperature for 2 hours. Methanol (0.5 ml) was added to destroy excess reagent. The reaction mixture was partitioned between dichloromethane (3×5 ml) and saturated NaCl (aq) (50 ml). The pooled organic layers were dried over anhydrous Na2SO4 and flash evaporated to dryness (dry weight=0.63, 0.81, 1.0 and 1.4 g respectively). Purification over a column of 50 g E. Merck silica gel 60 (43-60 μm particle size) in 40-80% acetone/hexane stepwise gradients yielded 0.43, 0.33, 0.29 and 0.56 g of the respective esters.

후처리

  1. customto destroy excess reagent
  2. customThe reaction mixture was partitioned between dichloromethane (3×5 ml) and saturated NaCl (aq) (50 ml)
  3. dry with materialThe pooled organic layers were dried over anhydrous Na2SO4 and flash
  4. customevaporated to dryness (
  5. customdry weight=0.63, 0.81, 1.0 and 1.4 g respectively)
  6. customPurification over a column of 50 g E

출처 및 근거

ORD 기록
ord-30559a06ff8749fdb1c766b31f5aecc9
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242938

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