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 2365048Notes

Reaction equation

HRID 2365048 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

3

Reactant 1

HCID 54704545tert-Butyl (3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-3-hydroxypropyl)carbamate

Product 1

HCID 10061105Ethyl 5-{[(tert-butoxy)carbonyl]amino}-3-oxopentanoateYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of [3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-3-hydroxy-propyl]-carbamic acid tert-butyl ester (18.75 g, 50 mmol) in absolute ethanol (112 ml) was heated overnight at 70° C. The mixture was concentrated under reduced pressure to give 5-tert-butoxycarbonylamino-3-oxo-pentanoic acid ethyl ester (14 g, 98%) as a yellow oil which was used as such.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3654842dd66f488490c47a502f32d51e
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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