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

HRID 535774ノート

反応式

HRID 535774 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b96182d44bfe4eb3b6aa70a66e47e755
出典データセット
uspto-grants-2014_10
特許番号
US08859556B2

反応ノート

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