Lithium Hydroxide → HCID 178486061, compound

HRID 1063627Notes

Reaction equation

HRID 1063627 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14])[CH2:9][CH2:8]1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[C:18]([O:17][C:15]([N:13]([CH3:14])[C@H:10]1[CH2:11][CH2:12][C@H:7]([O:6][CH2:5][CH2:4][C:3]([OH:22])=[O:2])[CH2:8][CH2:9]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 178500918HCID 178500918, compound

Product 1

HCID 178486061HCID 178486061, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.3 g (48.5 mmol) of trans-3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyloxy]-propionic acid methyl ester in 485 mL of THF were treated with 485 mL of 1M LiOH at RT for 1 h. The solution was acidified by adding 1M KHSO4, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The crude product was triturated with n-heptane to give trans-3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyloxy]-propionic acid as white solid, MS: 300 (M−H)−.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude product was triturated with n-heptane

Sources & evidence

ORD record
ord-76cc724ed9fd4c4cb9ff8dbcf4ccf024
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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