Hydrochloric Acid → HCID 86273512, compound

HRID 1777265Notes

Reaction equation

HRID 1777265 reaction equation
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:13][C@@H:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]4[CH2:26][N:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=5)[CH2:24]4)[CH:15]=3)[C@@:11]([C@H:34]([OH:36])[CH3:35])([CH3:33])[CH2:10]2)=[O:8])[CH2:4][O:3]1.Cl>O1CCCC1>[OH:36][C@@H:34]([C@@:11]1([CH3:33])[C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:24][N:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:26]3)[CH:15]=2)[CH2:13][N:9]([C:7](=[O:8])[C@@H:5]([OH:6])[CH2:4][OH:3])[CH2:10]1)[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 90416900HCID 90416900, compound

Product 1

HCID 86273512HCID 86273512, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R)-1-[(3S,4S)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]carbonyl}-4-(4-methoxy-3-{[1-pyridin-2-ylazetidin-3-yl]oxy}phenyl)-3-methylpyrrolidin-3-yl]ethanol (22.1 mg) in tetrahydrofuran (2 mL) is added aqueous 1.0 M HCl (1 mL). Stir overnight at room temperature. Add aqueous 1.0 M HCl (1 mL) and stir for additional 8 hours. Neutralize with aqueous 1.0 M NaOH, extract with ethyl acetate, dry and evaporate to provide the title compound (18.2 mg). MS (ES+)=472 (M+1).

Workup

  1. extractionNeutralize with aqueous 1.0 M NaOH, extract with ethyl acetate
  2. customdry
  3. customevaporate

Sources & evidence

ORD record
ord-c65ceb4acc2f42a19a9741b33e76d474
Source dataset
uspto-grants-2016_02
Patent number
US09266859B2

Reaction notes

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