Acetic Acid → HCID 131710910, compound

HRID 2072486Notes

Reaction equation

[ClH:1].[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@@H:9](O)[C@H:8]([CH2:14][N:15]1[CH2:31][CH2:30][C:18]3([N:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:21][NH:20][C:19]3=[O:29])[CH2:17][CH2:16]1)[CH2:7][CH2:6]2.C(O)(=O)C.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[ClH:1].[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:14][N:15]1[CH2:31][CH2:30][C:18]3([N:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:21][NH:20][C:19]3=[O:29])[CH2:17][CH2:16]1)[CH2:7][CH2:6]2

Participants

Conditions

Temperature: 25 °C

Procedure

Finely-ground trans-8-[(6-fluoro-1,2,3,4-tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]-decan-4-one (3g, see example 116) is added in small portions to a rapidly stirred acid solution comprising 20 ml acetic acid containing 20% v/v sulfuric acid maintained at 25° C. The resulting light-brown solution is stirred overnight at room temperature under nitrogen. The dehydration mixture is then gently warmed on a steam bath for 10 minutes. The warm solution is poured into ice-water (400 ml) and the resulting suspension basified with solid sodium bicarbonate. Extraction with chloroform yields a tan solid (1.9 g. 66%) containing small amounts of three impurities detected by TLC analysis. High pressure liquid chromatography (HPLC) of this material on silica gel with ethyl acetate gives 1.5 g of the free base of the title compound as colorless prisms, melting point 186°-187° C.

Workup

temperatureThe dehydration mixture is then gently warmed on a steam bath for 10 minutes
extractionExtraction with chloroform
customyields a tan solid (1.9 g. 66%)
additioncontaining small amounts of three impurities

Sources & evidence

ORD record: ord-a6206c6c8bfe41e18ec1dd86505e0ebc
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04051248

Reaction notes

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