Cesium carbonate → HCID 67074619, compound

HRID 1944083Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C:9]2([CH2:11][CH2:10]2)[O:8][C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH:18]=2)[C@@H:6]1[O:32][C:33](=[O:35])[CH3:34])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[O:42]1[CH2:46][CH2:45][C@@H:44](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:43]1>CN(C=O)C.O>[C:33]([O:32][C@@H:6]1[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C:9]2([CH2:10][CH2:11]2)[O:8][C@H:7]1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][C@H:44]3[CH2:45][CH2:46][O:42][CH2:43]3)=[CH:29][CH:30]=2)[CH:18]=1)(=[O:35])[CH3:34]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (120 mg, 0.22 mmole) in DMF (3 mL), cesium carbonate (85 mg, 0.27 mmole), Toluene-4-sulfonic acid (R)-(tetrahydro-furan-3-yl)ester (65 mg, 0.27 mmole) was added at room temperature and heated at 60° C. for 6 hours. The reaction mixture was diluted with water (20 mL), and extracted with dichloromethane (2×50 mL). Crude (5S,6S,7R,8S)-5-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-4-oxaspiro[2.5]octane-6,7,8-triyl triacetate obtained after the removal of solvent used for next step without purification.

Workup

extractionextracted with dichloromethane (2×50 mL)

Sources & evidence

ORD record: ord-40c968a4103342dbb538bb7e4ae91fe4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394772B2

Reaction notes

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