Water → HCID 67160567, compound

HRID 70310Notes

Reaction equation

HRID 70310 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:7][CH2:6][CH:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:31]C)=[O:30])[CH:24]=3)=[CH:19][CH:18]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.O[Li].O.O>C1COCC1>[CH3:1][C:2]1([CH3:33])[CH2:3][CH2:4][CH:5]([N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([OH:31])=[O:30])[CH:24]=3)=[CH:19][CH:18]=2)[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67160183HCID 67160183, compound

Product 1

HCID 67160567HCID 67160567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4′-[((4,4-dimethylcyclohexyl){[(1,1-dimethylethyl)oxy]carbonyl}-amino)methyl]-3-biphenylcarboxylate (0.850 g; 1.88 mmol), LiOH.H2O (0.395 g; 9.40 mmol), water (2 mL) and THF (20 mL) was heated under reflux for 24 h, cooled and concentrated in vacuo. The residue was partitioned between EtOAc/1N KHSO4, layers were separated and the organic layer was extracted with EtOAc (×2). combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a colorless foam. LC/MS (method E) tR 0.77 min; m/z 464 (M−H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between EtOAc/1N KHSO4, layers
  6. customwere separated
  7. extractionthe organic layer was extracted with EtOAc (×2)
  8. washcombined organics were washed (water, brine)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbcff5fecc7845ed9d026e45b2dfc32d
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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