Methanol → HCID 20578921, compound

HRID 1267534Notes

Reaction equation

HRID 1267534 reaction equation
O.[OH-].[Li+].[O:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]3[CH2:18][C@H:17]([N:19]([C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=4)[CH2:16][C@H:15]3[C:36]([O:38]C)=[O:37])=[CH:12][C:7]=2[O:6][CH2:5]1.CO>O>[O:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH2:13][N:14]3[CH2:18][C@H:17]([N:19]([C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=4)[CH2:16][C@H:15]3[C:36]([OH:38])=[O:37])=[CH:12][C:7]=2[O:6][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 20578938HCID 20578938, compound

Product 1

HCID 20578921HCID 20578921, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (17 mg, 0.405 mmol) was added to a solution of methyl(2S,4R)-1-(1,3-benzodioxol-5-ylmethyl)-4-[(3,3-dimethylbutanoyl)(3-methoxybenzyl)amino]tetrahydro-1H-2-pyrrolecarboxylate (10) (100 mg, 0.20 mmol) in 66% v/v methanol in water (1.0 mL). The mixture was stirred overnight at room temperature, then the solvent was removed under reduced pressure and the residue partitioned between dichloromethane (1.0 mL) and water (1.0 ml). The aqueous phase was acidified with 1.0 M aqueous citric acid and the two layers were vigorously stirred for 10 min at room temperature. The layers were separated and the aqueous layer was back-extracted with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and evaporated under reduced pressure to give the title acid (11) (70 mg, 72%) as an off-white solid:

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue partitioned between dichloromethane (1.0 mL) and water (1.0 ml)
  3. stirringthe two layers were vigorously stirred for 10 min at room temperature
  4. customThe layers were separated
  5. extractionthe aqueous layer was back-extracted with dichloromethane
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-586bda56bc1e4fc6bfa57ad09d2570fa
Source dataset
uspto-grants-2003_04
Patent number
US06552016B1

Reaction notes

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