Hydrochloric Acid → HCID 86697375, compound

HRID 237706Notes

Reaction equation

HRID 237706 reaction equation
[Li+].[OH-].[C:3]([C:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]3[C:17]=2[CH2:18][CH2:19][C@H:20]3[O:26][C:27]2[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([O:37]C)=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=2)=[C:11]([CH3:41])[CH:10]=1)([CH3:7])[CH3:6])#[N:4].Cl>O1CCCC1>[C:3]([C:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]3[C:17]=2[CH2:18][CH2:19][C@H:20]3[O:26][C:27]2[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=2)=[C:11]([CH3:41])[CH:10]=1)([CH3:7])[CH3:6])#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86697140HCID 86697140, compound

Product 1

HCID 86697375HCID 86697375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous LiOH solution (500 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(4-(2-cyanopropan-2-yloxy)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (130 mg) in tetrahydrofuran (2 mL). The mixture is stirred at room temperature for 48 hours. 1 N Hydrochloric acid (500 μL) is added and the residue is purified by HPLC on reversed phase. The product thus obtained is chromatographed on silica gel (petrole ether/ethyl acetate 80:20→20:80) to give the title compound. Yield: 23 mg; LC (method 12): tR=0.67 min; Mass spectrum (ESI+): m/z=516 [M+H]+.

Workup

  1. customthe residue is purified by HPLC on reversed phase
  2. customThe product thus obtained
  3. customis chromatographed on silica gel (petrole ether/ethyl acetate 80:20→20:80)

Sources & evidence

ORD record
ord-ff8048dbb76b40ac89cfe80b3b108de9
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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