Hydrochloric Acid → HCID 67464939, compound

HRID 1619939Notes

Reaction equation

C(=O)=O.CCO.[CH2:7]([N:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23](=[O:26])[CH2:24][CH3:25])=[CH:22][C:17]=2[O:16][C:15]1=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[CH:29]([CH2:34][CH2:35][CH3:36])[C:30]([O:32][CH3:33])=[O:31].Cl>C1COCC1>[CH2:7]([N:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23](=[O:26])[CH:24]([CH:29]([CH2:34][CH2:35][CH3:36])[C:30]([O:32][CH3:33])=[O:31])[CH3:25])=[CH:22][C:17]=2[O:16][C:15]1=[O:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: -2 °C

Procedure

200 mL (0.5 mol/l in toluene, 100 mmol) bis-(trimethylsilyl)-potassium amide in 1.50 L THF are placed under protective gas and cooled to −60° C. with dry ice/EtOH. 20 g (71 mmol) of 3-benzyl-6-propionyl-3H-benzoxazol-2-one dissolved in 500 mL THF are slowly added dropwise. The reaction mixture is stirred for 30 min at −2° C. and then cooled to −60° C. again. 20 g (83 mmol) methyl 2-iodo-pentanoate are added and the mixture is stirred for 45 min at −60° C. Then the reaction mixture is combined with 500 mL of 2M HCl and extracted at RT with diethyl ether. The organic phase is washed with saline solution, suction filtered through cellulose and the solv. is eliminated i.V. The residue is purified through silica gel (DCM/MeOH)

Workup

additionare slowly added dropwise
temperaturecooled to −60° C. again
stirringthe mixture is stirred for 45 min at −60° C
extractionextracted at RT with diethyl ether
washThe organic phase is washed with saline solution, suction
filtrationfiltered through cellulose
customThe residue is purified through silica gel (DCM/MeOH)

Sources & evidence

ORD record: ord-054ae8764563434795eab3c692a6f368
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772323B2

Reaction notes

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