1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

HRID 535774노트

반응식

HRID 535774 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[CH3:29][NH:30][O:31][CH3:32].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:32][O:31][N:30]([CH3:29])[C:10](=[O:12])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13]([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

생성물 1

HCID 21305336Tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (CAS 102185-35-3, 500 mg, 2.16 mmol) in DCM (5 mL) was added EDCI (CAS 25952-53-8, 497 mg, 2.59 mmol) and stirred for 10 min at rt. A solution of N,O-dimethylhydroxylamine hydrochloride (CAS 6638-79-5, 253 mg, 2.59 mmol) and DIPEA (0.429 mL, 2.59 mmol) in DCM (5 mL) was added and the reaction mixture was left to stir at rt over a weekend. The mixture was diluted with DCM (30 mL) and extracted with saturated aq NaHCO3 (50 mL). The organic phase was washed with water before being dried over MgSO4 and filtered. The solvent was removed in vacuo to give tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (466 mg, 79%).

후처리

  1. waitthe reaction mixture was left
  2. stirringto stir at rt over a weekend
  3. extractionextracted with saturated aq NaHCO3 (50 mL)
  4. washThe organic phase was washed with water
  5. dry with materialbefore being dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-b96182d44bfe4eb3b6aa70a66e47e755
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859556B2

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