Methanol → HCID 86757908, compound

HRID 279687Notes

Reaction equation

HRID 279687 reaction equation
C([O:3][C:4](=[O:33])[C@@H:5]([O:30][CH2:31][CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23](OC(C)(C)C)=O)=[CH:9][CH:8]=1)C.[OH2:34].[OH-:35].[Li+].ClCCl.CO>O>[C:16]([O:34][C:12]([C:7]1[CH:8]=[CH:9][C:23]([NH:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:30][CH2:31][CH3:32])[C:4]([OH:3])=[O:33])=[CH:12][CH:11]=2)=[CH:5][CH:6]=1)=[O:35])([CH3:21])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 69904847HCID 69904847, compound

Product 1

HCID 86757908HCID 86757908, compoundYield 140,426.703%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-{4-[-(tert-Butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester (27 g; 0.06 mmole) was dissolved in TBF (250 ml), and water (250 ml) was added during followed by addition of lithium hydroxide hydrate (3.75 g; 0.089 mmole) dissolved in a small amount of water. The reaction mixture was stirred at room temperature overnight and then concentrated by evaporation The residue was washed once with ethyl acetate. The water phase was acidified upon cooling with hydrochloric acid (2M) and extracted with ethyl acetate. The organic phase was washed with brine dried with magnesium sulfate and evaporated. The residue was redissolved in dichloromethane and chromatography on silica using a gradient system of dichloromethane: methanol (0-100%) gave 21.3 g (83% yield) 3-{4-[2-(4-tert-butoxycarbonylamiinophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid.

Workup

  1. concentrationconcentrated by evaporation The residue
  2. washwas washed once with ethyl acetate
  3. temperatureupon cooling with hydrochloric acid (2M)
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. dissolutionThe residue was redissolved in dichloromethane

Sources & evidence

ORD record
ord-3aeeb9539a65441aa3d3aee54298a876
Source dataset
uspto-grants-2002_03
Patent number
US06362360B1

Reaction notes

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