Furfuryl Alcohol → HCID 56928393, compound

HRID 330843Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].[CH2:8]([NH:10][C:11](=[O:29])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)[CH3:13])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:8]([NH:10][C:11](=[O:29])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]2[CH:23]=[CH:24][C:25]([O:7][CH2:6][C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)[CH3:13])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To 0.015 g (0.15 mmol) furan-2-ylmethanol in 0.75 mL THF are added 0.03 g (0.10 mmol) N-Ethyl-2-[4-(4-hydroxy-phenylethynyl)-phenyl]-propionamide (XVIII.2) and 40 mg polymer-bound triphenylphosphine (3 mmol/g resin). The mixture is cooled to 0° C. and 0.03 g (0.15 mmol) di-tert-butyl azodicarboxylate dissolved in 0.5 mL THF are added. The mixture is stirred over night at rt. After that time additional 0.03 g (0.15 mmol) di-tert-butyl azodicarboxylate dissolved in 0.5 mL THF are added and stirring is continued over night. Subsequently the mixture is filtered (Alox), washed (DMF/MeOH 9:1) and concentrated. The residue is dissolved in DMF and the desired product was purified using RP-HPLC (narrow gradient, water/MeOH+0.1% TFA).

Workup

additionare added
additionare added
stirringstirring
waitis continued over night
filtrationSubsequently the mixture is filtered (Alox)
washwashed (DMF/MeOH 9:1)
concentrationconcentrated
dissolutionThe residue is dissolved in DMF
customthe desired product was purified

Sources & evidence

ORD record: ord-3dc897e7c99d4f3ba11d71ea75107495
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877754B2

Reaction notes

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