tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamate → Ethyl 5-{[(tert-butoxy)carbonyl]amino}-3-oxopentanoate

HRID 2365038Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10](=[C:12]1C(=O)O[C:15](C)([CH3:19])[O:14][C:13]1=[O:21])[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[CH2:15]([O:14][C:13](=[O:21])[CH2:12][C:10](=[O:11])[CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:22])[CH3:19]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred solution of [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxin-5-ylidene)-3-hydroxy-propyl]-carbamic acid tert-butyl ester in absolute ethanol (112 ml) was heated to reflux at 70° C. overnight, and cooled to room temperature. The mixture was filtered and concentrated under reduced pressure to give 5-tert-butoxycarbonylamino-3-oxo-pentanoic acid ethyl ester (11.22 g, 87%) as a white solid.

Workup

temperaturecooled to room temperature
filtrationThe mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3a061270c9544016b70cd73cd67ae48b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697692B2

Reaction notes

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