HCID 69344213, compound → HCID 69344742, compound

HRID 857102Notes

Reaction equation

[CH3:1][C:2]1([CH3:41])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([N:35]5[CH2:39][CH2:38][NH:37][C:36]5=[O:40])[CH:30]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1>C1COCC1>[CH3:1][C:2]1([CH3:41])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:16])[CH2:13][NH:14][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([N:35]4[CH2:39][CH2:38][NH:37][C:36]4=[O:40])[CH:32]=[CH:33][CH:34]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-(6-{4-[3-(2-oxoimidazolidin-1-yl)phenyl]butoxy}hexyl)-1,3-oxazolidin-2-one (113 mg) was stirred in THF (8 ml) while purging with a vigorous stream of nitrogen for 3 min. Potassium trimethylsilanolate (285 mg) was added and the mixture was stirred at 80° C. under nitrogen for 0.75 h. MeOH (10 ml) was added and then the solvents were removed under reduced pressure. The residue was dissolved in MeOH and applied to a silica Bond Elut cartridge (10 g) which was preconditioned in CH2Cl2 eluting with CH2Cl2, 5% MeOH—CH2Cl2, 2% increasing to 10% 2M NH3 in MeOH—CH2Cl2 to give the title compound (39 mg). LCMS RT=2.94 min

Workup

customwhile purging with a vigorous stream of nitrogen for 3 min
additionPotassium trimethylsilanolate (285 mg) was added
additionMeOH (10 ml) was added
customthe solvents were removed under reduced pressure
dissolutionThe residue was dissolved in MeOH
temperatureincreasing to 10% 2M NH3 in MeOH—CH2Cl2

Sources & evidence

ORD record: ord-96e89e6f80134b05a41382255f57572d
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144908B2

Reaction notes

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