Lithium Hydroxide → HCID 19417685, compound

HRID 260010Notes

Reaction equation

HRID 260010 reaction equation
C([O:8][C:9](=[O:28])[CH2:10][N:11]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][C:13]1([O:19][CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)C1C=CC=CC=1.[Li+].[OH-]>C1COCC1.O>[C:24]([O:23][C:21]([N:11]([CH2:12][C:13]1([O:19][CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][C:9]([OH:28])=[O:8])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53789576HCID 53789576, compound2×

Product 1

HCID 19417685HCID 19417685, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The latter ester (1.25 g) was dissolved in THF/H2O (3:2,25 mL). After LiOH (0.30 g, 12.9 mol) was added, the mixture was stirred at room temperature for 20 h. The mixture was concentrated under reduced pressure. H2O (13 mL) was added to the residue. The resulting solution was washed with EtOAc, rendered acidic by the addition of aqueous 1M HCl and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried (Na2SO4) and concentrated to dryness to give the acetic acid derivative, 2-{tert-butyloxycarbonyl[(1-methoxycyclohexyl)methyl]amino}acetic acid (0.56 g, 72% yield from 1-methoxycyclohexanemethanamine); 1H NMR(CDCl3) δ4.04 (s,0.6H), 3.94 (s,1.4H), 3.41 (s,1.4H), 3.35 (s,0.6H), 3.23 (s,1.9H), 3.18 (s,1.1H), 1.78-1.22 (m,20H); FAB mass spectrum, m/z: 302 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionH2O (13 mL) was added to the residue
  3. washThe resulting solution was washed with EtOAc
  4. additionrendered acidic by the addition of aqueous 1M HCl
  5. extractionextracted with EtOAc (3×)
  6. washThe combined EtOAc extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32ed7664ad4243838e349ae1f8079b62
Source dataset
uspto-grants-1996_06
Patent number
US05523315

Reaction notes

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