Lithium Hydroxide → HCID 178525562, compound

HRID 1713882Notes

Reaction equation

HRID 1713882 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH2:24][C:25]([O:27]C)=[O:26])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]2)=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178500686HCID 178500686, compound

Product 1

HCID 178525562HCID 178525562, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [trans-4-(4-{[(benzyloxy)carbonyl]amino}phenyl)cyclohexyl]acetate (3.34 g, 8.76 mmol) in THF (42 mL) and MeOH (42 mL) was added 0.6M aqueous lithium hydroxide (43.6 mL, 26.27 mmol) and the mixture stirred at ambient temperature for 18 hours. The mixture was partitioned between EtOAc (200 mL) and 1M HCl (100 mL). The organic phase was concentrated in vacuo and the residue partitioned between EtOAc (300 mL) and brine (20 mL). The organic phase was dried (MgSO4), filtered and evaporated to give the title compound (3.19 g, 99%) as a white solid; 1H NMR (CDCl3) δ 1.05-1.15 (2H, m), 1.36-1.46 (2H, m), 1.74-1.87 (5H, m), 2.22 (2H, d), 2.34-2.41 (1H, m), 5.13 (2H, s), 6.58 (1H, s), 7.07 (2H, d), 7.21 (3H, t), 7.28-7.35 (4H, m); MS m/e (MH)+ 368

Workup

  1. customThe mixture was partitioned between EtOAc (200 mL) and 1M HCl (100 mL)
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe residue partitioned between EtOAc (300 mL) and brine (20 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4b02a3ace90c40beb9e05360004085a8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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