Methyl chloroformate → (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate

HRID 1619509노트

반응식

HRID 1619509 반응식
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[CH3:31][O:30][C:29]([NH:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])=[O:32]

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

생성물 1

HCID 67607568(R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate수율 40.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) in DCM (5 ml), were added triethylamine (188 μl, 1.35 mmol) and methyl carbonochloridate (41.7 μl, 0.54 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc and washed with water and brine. The organic phase was dried over Na2SO4 and evaporated to obtain (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate (58.0 mg; 40% yield). The compound was used in the next step without any further purification.

후처리

  1. customthe solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-b57e3d1877d346b2bc54c2fe27955ffa
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772314B2

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