Ammonia → Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamate

HRID 227933노트

반응식

HRID 227933 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=O)([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.O[N:24]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([NH2:24])=[O:22])([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

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

생성물 1

HCID 23150697Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamate수율 89.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-Benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (998 mg) was suspended in acetonitrile (20 mL). While the suspension was chilled in an ice bath, N-hydroxybenzotriazole (605 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (757 mg) were sequentially added. The mixture was stirred at room temperature for 4 hours and was left overnight. Subsequently, 25% aqueous ammonia (1.80 mL) was added while the reaction vessel was chilled in an ice bath. The mixture was then stirred at room temperature for 1 hour. The insoluble material was filtered and washed sequentially with acetonitrile and dichloromethane. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:ethyl acetate) to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxamide (889 mg).

후처리

  1. temperatureWhile the suspension was chilled in an ice bath
  2. waitwas left overnight
  3. temperaturewas chilled in an ice bath
  4. stirringThe mixture was then stirred at room temperature for 1 hour
  5. filtrationThe insoluble material was filtered
  6. washwashed sequentially with acetonitrile and dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (eluant:ethyl acetate)

출처 및 근거

ORD 기록
ord-ec25fb55fb3b45baa7db8d7d33612a69
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560569B2

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