Diisopropylethylamine → (R)-tert-butyl 3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamate

HRID 1971110노트

반응식

HRID 1971110 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN.C[CH2:21][N:22](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[CH3:14][C:13]([CH3:16])([CH3:15])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]([NH:22][CH3:21])=[O:11]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6364545Methylamine hydrochlorideHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

생성물 1

HCID 57635611(R)-tert-butyl 3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamate수율 77.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a cold solution of (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (0.50 g, 2.16 mmol) in acetonitrile (8 mL) was added methylamine hydrochloride (0.48 g, 7.13 mmol), followed by DIEA (1.67 g, 12.9 mmol). The resulting mixture was stirred for 20 min and TBTU (0.76 g, 2.37 mmol) was added and the stirring continued overnight. The mixture was concentrated, diluted with EtOAc (30 mL) and washed successively with aqueous 5% KHSO4, saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4, filtered and concentrated to provide Intermediate 30A (0.41 g, 77%).

후처리

  1. customthe stirring continued overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with EtOAc (30 mL)
  4. washwashed successively with aqueous 5% KHSO4, saturated NaHCO3 solution and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-11760df5ec0a4cd9b722c20f57cf99f3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431565B2

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