Hydrochloric Acid → HCID 49806372, compound

HRID 1615056Notes

Reaction equation

HRID 1615056 reaction equation
[CH:1]1([C:4]2[CH:41]=[CH:40][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:19][N:18]([C:20]([C:22]5[CH:27]=[C:26]([CH2:28][O:29][CH2:30][C@@H:31]6[CH2:35][O:34]C(C)(C)[O:32]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:38][CH3:39])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C1(C2C=CC(COC3C=CC(C4CN(C(C5C=C([C@H](C6COC(C)(C)O6)OC)C=CN=5)=O)C4)=CC=3OC)=CC=2)CC1.Cl>O1CCCC1>[CH:1]1([C:4]2[CH:41]=[CH:40][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:17][N:18]([C:20]([C:22]5[CH:27]=[C:26]([CH2:28][O:29][CH2:30][C@@H:31]([OH:32])[CH2:35][OH:34])[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:19]4)=[CH:12][C:11]=3[O:38][CH3:39])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59633965HCID 59633965, compoundHCID 66786530HCID 66786530, compound

Product 1

HCID 49806372HCID 49806372, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)pyridin-2-yl]-methanone prepared in (8) in THF (10 mL) was added 1 N hydrochloric acid (5 mL). The reaction mixture was stirred at RT for 3 hr. The reaction mixture was quenched with aqueous 1 N NaOH and saturated aqueous NaHCO3. The mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by preparative thin-layer chromatography (Developing solvent: chloroform/methanol=8/1) to give the title compound (0.30 g, 38%).

Workup

  1. customThe reaction mixture was quenched with aqueous 1 N NaOH and saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative thin-layer chromatography (Developing solvent: chloroform/methanol=8/1)

Sources & evidence

ORD record
ord-69f9f65eb3cc4c0d9adf75018984b4f8
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

Loading…