HCID 58764094, compound → HCID 58764019, compound

HRID 2387032Notes

Reaction equation

HRID 2387032 reaction equation
[CH:1]1([C:6]2([CH2:26][CH2:27][C:28]3[CH:44]=[CH:43][C:31]([O:32][CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C)=[C:30]([CH2:45][CH3:46])[CH:29]=3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[C:8](=[O:25])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[NH2:35][CH2:34][CH2:33][O:32][C:31]1[CH:43]=[CH:44][C:28]([CH2:27][CH2:26][C:6]2([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[O:7][C:8](=[O:25])[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)=[C:10]([OH:12])[CH2:11]2)=[CH:29][C:30]=1[CH2:45][CH3:46]

Participants

4

Reactant 1

HCID 58764094HCID 58764094, compound

Product 1

HCID 58764019HCID 58764019, compoundYield 111.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-[4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-ethylphenoxy]ethylcarbamate (Example A(70)) (250 mg) was dissolved in 4N HCl in dioxane (10 ml) and stirred at room temperature for 12 hrs. Upon completion the mixture was concentrated and azeotroped several times with dichloromethane to afford the title compound as a white solid (235 mg). 1H NMR (300 MHz, MeOD): δ 1.18 (t, J=7.56 Hz, 3 H) 1.32-2.35 (m, 11 H), 2.59-2.85 (m, 15 H), 2.92 (dd, J=116.54 Hz, 1 H), 4.05 (t, J=7.54 Hz, 2 H), 6.55 (d, J=1.56 Hz, 1 H), 6.65 (d, J=1.56 Hz, 1 H), 6.95 (s, 1 H), 6.99 (s, 1 H).

Workup

  1. concentrationUpon completion the mixture was concentrated
  2. customazeotroped several times with dichloromethane

Sources & evidence

ORD record
ord-60ec15cb94f04360a5ab187a3c7b91bb
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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