Hydrochloric Acid → HCID 57709194, compound

HRID 547126Notes

Reaction equation

Cl.C[O:3][C:4](=[O:40])[C@@H:5]([NH2:39])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH2:36][CH3:37])([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29]([OH:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:23]([CH3:35])[CH:22]=3)[CH2:19][CH3:20])=[CH:14][C:13]=2[CH3:38])=[CH:8][CH:7]=1>CC(C)=O>[NH2:39][C@@H:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH2:19][CH3:20])([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29]([OH:34])[C:30]([CH3:31])([CH3:32])[CH3:33])=[C:23]([CH3:35])[CH:22]=3)[CH2:36][CH3:37])=[CH:14][C:13]=2[CH3:38])=[CH:10][CH:11]=1)[C:4]([OH:40])=[O:3]

Participants

Conditions

Temperature: 140 °C

Procedure

A 4 N hydrochloric acid aqueous solution (0.80 mL) was added to a solution of the mixture containing (S)-amino-(4′-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2′-methyl-biphenyl-4-yl)-acetic acid methyl ester (220 mg) in acetone (0.60 mL), and the mixture was stirred with microwave heating at 140° C. for 10 minutes. The reaction mixture was purified by high performance liquid chromatography (GL Sciences Inertsil ODS-3, 20 mm I.D.×150 mm, methanol:water=20:80 to 100:0, 20 mL/min) and concentrated under reduced pressure to give the target compound as a white solid (14.0 mg, 36% in two steps).

Workup

customThe reaction mixture was purified by high performance liquid chromatography (GL Sciences Inertsil ODS-3, 20 mm I.D.×150 mm, methanol:water=20:80 to 100:0, 20 mL/min)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0554c1e815cd45aa858073c1751bfe50
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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