Citric Acid → HCID 53318971, compound

HRID 1181599Notes

Reaction equation

[OH:1][C@H:2]([CH2:21][NH:22][C:23]([CH3:36])([CH3:35])[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH2:3][O:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1C=CC(C#N)=CC=1)[CH3:6].[OH-].[K+].O.[C:40](O)(=O)[CH2:41][C:42]([CH2:47][C:48](O)=O)([C:44]([OH:46])=[O:45])O>C(O)CO>[OH:1][C@H:2]([CH2:21][NH:22][C:23]([CH3:35])([CH3:36])[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH2:3][O:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:40]=[CH:41][C:42]([C:44]([OH:46])=[O:45])=[CH:47][CH:48]=1)[CH3:6]

Participants

Conditions

Temperature: 160 °C

Procedure

2′-[1-[(2R)-2-Hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]biphenyl-4-carbonitrile (1.0 g) obtained in Example 7, Step 2 was dissolved in ethylene glycol (15 ml). Potassium hydroxide (2.76 g) was added and the mixture was stirred overnight at 160° C. The reaction mixture was allowed to return to room temperature, a small amount of water was added and 10% aqueous citric acid was added to adjust the mixture to pH 4-5. The precipitated solid was collected by filtration to give the title compound (924 mg).

Workup

customto return to room temperature
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-7ff7b41997a24d49a521598b6edfa2f6
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285572B2

Reaction notes

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