Hydrochloric Acid → HCID 86700819, compound

HRID 2406554Notes

Reaction equation

HRID 2406554 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@:15]3([CH2:25][C:26]4[CH:27]=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=4)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[OH-].[Na+].Cl.CC#N.O>O1CCCC1>[Cl:32][C:29]1[N:28]=[CH:27][C:26]([CH2:25][C@@:15]2([O:14][C:12]3[CH:11]=[CH:10][C:9]4[C@H:5]([CH2:4][C:3]([OH:33])=[O:2])[CH2:6][O:7][C:8]=4[CH:13]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[F:24])[CH2:17][CH2:16]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 86700787HCID 86700787, compound

Product 1

HCID 86700819HCID 86700819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{(S)-6-[(R)-(6-Chloro-pyridin-3-ylmethyl)-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzo-furan-3-yl}-acetic acid methyl ester (18.6 mg) is dissolved in tetrahydrofuran (4 mL) and 1N aqueous sodium hydroxide solution (0.4 mL) is added. The mixture is stirred at room temperature overnight and then acidified with 1N aqueous hydrochloric acid (0.4 mL). The solution is submitted to HPLC on reversed phase (MeCN/water) to give the title compound. LC (method 6): tR=0.66 min; Mass spectrum (ESI−): m/z=452/454 (Cl) [M−H]−.

Sources & evidence

ORD record
ord-10a42ec768484b68ac30cc0c0aa0ea1e
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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