Benzyl Alcohol → 3-Benzyloxycarbonylamino-6-methyl-2-pyridone

HRID 567798노트

반응식

HRID 567798 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5](C(O)=O)[C:6](=[O:8])[N:7]=1.C([N:14]([CH2:17]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([NH:14][C:17](=[O:26])[O:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471Triethylamine2회HCID 199401P,P-Diphenylphosphinic azide2회HCID 184709516-Methyl-2-oxo-2,3-dihydropyridine-3-carboxylic acid

생성물 1

HCID 100838403-Benzyloxycarbonylamino-6-methyl-2-pyridone수율 65.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A suspension of 6-methyl-2-oxo-2,3-dihydro-3-pyridinecarboxylic acid (20 g, 0.13 mol) in dioxan (400 ml) was treated with triethylamine (22 ml, 0.15 mol) followed by diphenylphosphoryl azide (30.8 ml, 0.14 mol) and heated under reflux for 2 hr. A further portion of diphenylphosphoryl azide (3 ml) and triethylamine (2 ml) were added and heated under reflux for a further 1 hr. The resultant mixture was then treated with benzyl alcohol (18.8 ml, 0.18 mol) and heated under reflux for 18 hr. The resultant mixture was cooled, evaporation of the solvent gave a crude solid which was triturated with water. The solid was collected by filtration, washed with HCl (1N, 300 ml) then water. The solid was triturated with diethyl ether, filtered, washed with diethyl ether and dried to give the desired product (22 g, 65%). 1H NMR (CDCl3) δ 1.20 (s, 1H), 2.30 (s, 3H), 5.20 (s, 2H), 6.05 (d, 1H), 7.40 (m, 5H), 7.70 (s, 1H), 8.00 (d, 1H). LRMS m/z=259.2 (M+1)+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. temperatureheated
  4. temperatureunder reflux for a further 1 hr
  5. temperatureheated
  6. temperatureunder reflux for 18 hr
  7. customevaporation of the solvent
  8. customgave a crude solid which
  9. customwas triturated with water
  10. filtrationThe solid was collected by filtration
  11. washwashed with HCl (1N, 300 ml)
  12. customThe solid was triturated with diethyl ether
  13. filtrationfiltered
  14. washwashed with diethyl ether
  15. customdried

출처 및 근거

ORD 기록
ord-5695b25b06f248f293be554a7b4e8636
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180627B2

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