Hydrochloric Acid → HCID 86676914, compound

HRID 332701Notes

Reaction equation

HRID 332701 reaction equation
C(OC(=O)[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]2[O:31][CH2:30][CH2:29][O:28]2)[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.Cl.O1CCOCC1>CO>[CH3:29][O:28][CH:27]([O:31][CH3:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:17]1[CH:16]=[C:15]([CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH2:7])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71113126HCID 71113126, compound

Product 1

HCID 86676914HCID 86676914, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl((3-((5-(1,3-dioxolan-2-yl)pentyl)oxy)phenyl)(phenyl)-methyl)carbamate (0.483 g, 1.10 mmol) in methanol (4 mL), was added hydrogen chloride in dioxan (4 M, 4 mL, 16 mmol). The reaction was stirred at ambient temperature for 7 hours. The solvent was evaporated at reduced pressure, and the residue loaded onto an SCX-2 cartridge. The cartridge was eluted with methanol (eight column volumes) followed by ammonia/methanol. Fractions containing the product were combined and evaporated at reduced pressure to afford the title compound as a colourless oil (0.322 g, 85%).

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. washThe cartridge was eluted with methanol (eight column volumes)
  3. additionFractions containing the product
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-6bf3934fa2dd483bb14711fbee787e03
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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