Ethyl Acetate → HCID 178487960, compound

HRID 633803Notes

Reaction equation

[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]([OH:38])[CH:16]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[N:26]=3)[N:21]=[CH:20][C:19]=2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[OH:17])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:40](OCC)(=[O:42])C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][CH:15]2[CH:16]([C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[N:26]=4)[N:21]=[CH:20][C:19]=3[O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:17][C:40](=[O:42])[O:38]2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

N,N′-Carbonyldiimidazole (2.56 g, 15.83 mmol, 5.0 eq) is added at room temperature to a stirred solution of {trans-4-[3-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2,3-dihydroxy-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.70 g, 3.16 mmol, 1.0 eq) in toluene (150 mL). After 2 hours stirring at 70° C., solvent is removed and the crude is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford {trans-4-[5-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-[1,3]dioxolan-4-ylmethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (1.70 g, 96% yield).

Workup

customsolvent is removed
customthe crude is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record: ord-8c92898f9f0348139b6a362d96651e8e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321788B2

Reaction notes

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