Methanol → 2-{[(Benzyloxy)carbonyl]amino}-3-(1-methylcyclohexyl)propanoic acid

HRID 451786

Reaction equation

HRID 451786 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CO>O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1([CH3:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 59201682Methyl 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoate

Product 1

HCID 592017212-{[(Benzyloxy)carbonyl]amino}-3-(1-methylcyclohexyl)propanoic acidYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoate, 10.00 g of KOH, 100 mL of MeOH, and 20 mL of water was vigorously stirred at rt for 17 h. After methanol was evaporated under reduced pressure, the residue was diluted with water and extracted with Et2O (2×). The aqueous phase was treated with 100 mL of 2 NHCl, extracted with EtOAc (3×), and dried over Na2SO4. The extracts were evaporated under reduced pressure to afford 1.5150 g (36% in two steps) of 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoic acid. MS ESI +ve m/z 320 (M+H).

Workup

  1. customAfter methanol was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with Et2O (2×)
  4. additionThe aqueous phase was treated with 100 mL of 2 NHCl
  5. extractionextracted with EtOAc (3×)
  6. dry with materialdried over Na2SO4
  7. customThe extracts were evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b45424b9fb34b919301478106d6887d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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