Water → HCID 57190689, compound

HRID 987301Notes

Reaction equation

HRID 987301 reaction equation
[C:1]([O:5][C:6]([N:8](C)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][O:30][C:31](=[O:46])[CH:32]([O:41][CH2:42][CH2:43][O:44][CH3:45])[CH2:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:29][O:30][C:31](=[O:46])[CH:32]([O:41][CH2:42][CH2:43][O:44][CH3:45])[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:14][CH:13]=2)=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22988738HCID 22988738, compoundHCID 54228329HCID 54228329, compound

Product 1

HCID 57190689HCID 57190689, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[4-{tert-Butoxycarbonyl(methyl)amino}phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.50 g; 1.26 mmole), 3-(4-hydroxyphenyl)-2-(2-methoxyethoxy)propanoic acid methyl ester(0.32 g; 1.26 mmole) and potassium carbonate (0.35 g; 2.64 mmole) were mixed in acetonitrile (20 ml) and refluxed over night. Water was added, acetonitrile evaporated and the residue extracted three times with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated. Purification of the crude product with preparativ HPLC (Kromasil C8, 7 μm, 50×250 mm) using acetronitrile (50-70%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.34 g (58% yield) of 3-[4-(2-(4-tert-butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2-methoxyethoxy)propanoic acid methyl ester

Workup

  1. temperaturerefluxed over night
  2. customacetonitrile evaporated
  3. extractionthe residue extracted three times with ethyl acetate
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. customevaporated
  6. customPurification of the crude product with preparativ HPLC (Kromasil C8, 7 μm, 50×250 mm)

Sources & evidence

ORD record
ord-4d8e59b88b3c465894ff87950a3f1345
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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