Propionic Acid → 5-[5-(Benzyloxycarbonyl)furan-2-yl]-4-tert-butoxycarbonyl-4-pentenoic acid ethyl ester

HRID 517344Notes

Reaction equation

HRID 517344 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]([CH:9]([C:11]1[O:12][C:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:14][CH:15]=1)O)=[CH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:27]([O-:32])([O-])[O:28][CH2:29][CH3:30].[C:33](O)(=O)CC>>[CH2:29]([O:28][C:27](=[O:32])[CH2:33][CH2:8][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:26])=[CH:9][C:11]1[O:12][C:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:14][CH:15]=1)[CH3:30]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 53630039EthylorthoformateHCID 866733232-{[5-(Benzyloxycarbonyl)furan-2-yl](hydroxy)methyl}prop-2-enoic acid tert-butyl ester

Product 1

HCID 779345225-[5-(Benzyloxycarbonyl)furan-2-yl]-4-tert-butoxycarbonyl-4-pentenoic acid ethyl ester

Conditions

Temperature
138 °C

Procedure

2-{[5-(Benzyloxycarbonyl)furan-2-yl](hydroxy)methyl}prop-2-enoic acid tert-butyl ester (90 mg, 0.25 mmol) was dissolved in ethyl orthoformate (2.0 mL, 10.9 mmol), propanoic acid (8 mg, 0.10 mmol) was added, and the mixture was stirred at 138° C. for 5 hours. The mixture was purified by silica gel column chromatography to give the title compound.

Workup

  1. customThe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-89259d6f251d48c1ba176b161723cf51
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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