Ammonia → 1,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

HRID 891696노트

반응식

HRID 891696 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:14]1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.N>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:12])[NH2:14])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycine

생성물 1

HCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate수율 24%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of N-(t-butoxycarbonyl)glycine (3.01 g, 17.2 mmol) in anhydrous methylene chloride (150 ml) were added 1-hydroxybenzotriazole (4.63 g, 34.3 mmol), WSC (6.60 g, 34.4 mmol) and 4-dimethylaminopyridine (210 mg, 1.72 mmol) in an ice bath. The mixture was stirred at room temperature under an atmosphere of nitrogen overnight. After checking the completion of the reaction, 28% aqueous ammonia solution was added thereto and resulting mixture was stirred for 15 minutes. After checking the completion of the reaction, the reaction mixture was partitioned between methylene chloride and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford (carbamoylmethyl)carbamic acid t-butyl ester (717.7 mg, yield 24%) as a colorless and transparent syrup.

후처리

  1. additionwas added
  2. customresulting mixture
  3. stirringwas stirred for 15 minutes
  4. customthe completion of the reaction
  5. customthe reaction mixture was partitioned between methylene chloride and saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-8310f699012c4c76983294feb0e71eee
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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