1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1-oxobutan-2-ylcarbamate
Reaction equation
[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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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%).
Workup
- waitthe reaction mixture was left
- stirringto stir at rt over a weekend
- extractionextracted with saturated aq NaHCO3 (50 mL)
- washThe organic phase was washed with water
- dry with materialbefore being dried over MgSO4
- filtrationfiltered
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-b96182d44bfe4eb3b6aa70a66e47e755
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859556B2
Reaction notes
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