Pyridine → Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

HRID 1377420노트

반응식

HRID 1377420 반응식
[CH3:1][C:2]([CH3:14])([O:4][C:5]([NH:7][CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[O:6])[CH3:3].N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CN(C1C=CN=CC=1)C.C1COCC1.CCOC(C)=O>[C:21]([O:13][CH:8]([NH:7][C:5]([O:4][C:2]([CH3:14])([CH3:1])[CH3:3])=[O:6])[C:9]([O:11][CH3:12])=[O:10])(=[O:23])[CH3:22]

참가 물질

7

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11106496Methyl 2-((tert-butoxycarbonyl)amino)-2-hydroxyacetate

생성물 1

HCID 10922855Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester수율 98%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the product of Example 1 (10.0 g, 48.8 mmol), pyridine (7.71 g, 97.6 mmol) and DMAP (300 mg, 2.5 mmol) in THF (50 ML) was added acetic anhydride (5.47 g, 53.6 mmol) slowly at room temperature. After stirring at ambient temperature for 3 hours, the reaction was diluted with EtOAc and washed successively with 1N NaHSO4 and sat'd NaHCO3. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure affording 11.8 g (98%) of product as a colorless oil.

후처리

  1. washwashed successively with 1N NaHSO4
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e4489cea09c34ad0913b3eaff51869af
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665598

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