N-(tert-butoxycarbonyl)glycine → Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate

HRID 1465454

반응식

HRID 1465454 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5](NCC)=[CH:4][CH:3]=1.[C:11]([NH:18][CH2:19][C:20]([OH:22])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Cl.[CH2:24]([N:26]=C=NCCCN(C)C)[CH3:25].C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]([NH:18][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:20]([NH:26][CH2:24][CH3:25])=[O:22])=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117456564-bromo-N-ethylaniline

생성물 1

HCID 86651843Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate수율 99%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-bromo-N-ethylaniline (1.28 g, 6.4 mmol), N-Boc-glycine (1.57 g, 9.0 mmol) in pyridine (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.47 g, 7.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 hrs. The reaction mixture was poured into a mixture of diluted aqueous sodium hydrogen carbonate solution and ethyl acetate. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate (2.255 g, yield 99%) as a yellow solid.

후처리

  1. stirringThe mixture was stirred
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-25a144044dc44926b0ad03b5e4a7d73f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999989B2

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