Hydrochloric Acid → HCID 86703895, compound

HRID 471463

Reaction equation

[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=4)[C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[O:36]1[C:38]2([CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH2:37]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O.O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:37][C:38]5([OH:36])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[CH:31][CH:30]=4)[C:21]([C:25]([F:26])([F:27])[F:28])=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

((1S,2S)-2-{4-[(R)-4-(4-Hydroxy-phenyl)-5-trifluoromethyl-indan-1-yloxy]-phenyl}-cyclopro-panecarboxylic acid ethyl ester (crude from step 2), 1,6-dioxa-spiro[2.5]octane (US2012/46304, 44 mg) and cesium carbonate (198 mg) are suspended in dry N,N-dimethylformamide and heated at 100° C. for 3 hours. The mixture is diluted with water, acidified with 0.2 M HCl solution and extracted with ethyl acetate. The combined organic extracts are concentrated under vacuum and the residue purified by flash chromatography (0-30% EtOAc in cyclohexane) ti give the title compound (yield 50 mg).

Workup

extractionextracted with ethyl acetate
concentrationThe combined organic extracts are concentrated under vacuum
customthe residue purified by flash chromatography (0-30% EtOAc in cyclohexane) ti

Sources & evidence

ORD record: ord-2ef9da7c07234a1bbac33a7b94f0ad9d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633182B2

Linked notes

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