Benzyl {2-[(tert-butoxycarbonyl)amino]-3-(methylamino)-3-oxopropyl}carbamate → 3-amino-N2-(tert-butoxycarbonyl)-N-methylalaninamide

HRID 1504820Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]([NH:24][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]([NH:24][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-(methylamino)-3-oxopropyl}carbamate (2.5 g, 7.4 mmol) in methanol (40 mL) was added palladium on carbon (0.25 g, 10% w/w). The mixture was stirred under a hydrogen atmosphere (50 psi) at 50° C. After 4 hours, the reaction mixture was filtered and concentrated under reduced pressure to afford 3-amino-N2-(tert-butoxycarbonyl)-N-methylalaninamide. MS ESI calc'd. for C9H20N3O3 [M+H]+ 218. found 218. 1H NMR (400 MHz, CD3OD) δ 4.06-4.02 (m, 1H), 2.93-2.82 (m, 2H), 2.76 (s, 3H), 1.47 (s, 9H).

Workup

filtrationthe reaction mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7fbfe7920a694e36806bfcc5eb7c7891
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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