Ethanolamine → HCID 131724837, compound

HRID 1816043Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]>C(O)CCC.C(OCC)(=O)C>[C:1]([OH:9])(=[O:2])[CH3:3].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][NH:4][CH2:3][CH2:1][OH:2])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethanolamine (0.07 ml) was added to a suspension of 2-chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 6e, 0.170 g) in n-butanol (5 ml) and heated at 100° C. in a sealed tube for 12 h. On cooling to ambient temperature the solution was diluted with ethyl acetate and extracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine, dried over magnesium sulfate and concentrated under reduced pressure. Purification by preparative reverse phase HPLC (eluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%) gave the title compound as the acetate salt (0.070 g).

Workup

temperatureOn cooling to ambient temperature the solution
extractionextracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification by preparative reverse phase HPLC (
washeluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%)

Sources & evidence

ORD record: ord-b9cc2fb17cae4d9bbc92e90178e69cac
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881754B2

Reaction notes

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