Sodium Hydroxide → 4-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 555673노트

반응식

HRID 555673 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22]C)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 23149677Methyl 4-{[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate

생성물 1

HCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid수율 91.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

Methyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate (64.3 g) was dissolved in ethanol (1100 mL). To this solution, a 1 mol/L aqueous solution of sodium hydroxide (1000 mL) was added and the mixture was stirred at 50° C. for 1 hour. Ethanol in the mixture was evaporated under reduced pressure and the residue was washed with diethylether (500 mL), followed by addition of concentrated hydrochloric acid to adjust the pH to acidic (pH 1). The resulting crystals were filtrated, washed with water, and dried under reduced pressure to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (56.1 g).

후처리

  1. customEthanol in the mixture was evaporated under reduced pressure
  2. washthe residue was washed with diethylether (500 mL)
  3. additionfollowed by addition of concentrated hydrochloric acid
  4. filtrationThe resulting crystals were filtrated
  5. washwashed with water
  6. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-aad614e5dd1b4d36b475426b42923532
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053465B2

반응 노트

불러오는 중…