Benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate → 3-amino-N2-(tert-butoxycarbonyl)-N,N-dimethylalaninamide

HRID 1504836Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH2:10][NH:11]C(=O)OCC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:11][CH2:10][C@@H:9]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate (5.5 g, 15 mmol) in methanol (100 mL) was added palladium on carbon (0.55 g, 10% w/w). The reaction mixture was stirred under a hydrogen (50 psi) atmosphere at 50° C. After 4 hours, the reaction mixture was filtered and concentrated under reduced pressure to afford 3-amino-N2-(tert-butoxycarbonyl)-N,N-dimethylalaninamide. MS ESI calc'd. for C10H22N3O3 [M+H]+ 232. found 232. 1H NMR (400 MHz, CD3OD) δ 4.59-4.46 (m, 1H), 2.91 (s, 3H), 2.86 (s, 3H), 2.75-2.72 (m, 1H), 2.71-2.69 (m, 1H) 1.43 (s, 9H).

Workup

filtrationthe reaction mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d21213e46c484473bceacdb7335e3879
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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