Methyl chloroformate → (S)-2-ethoxy-3-(4-[2-{4-(methoxycarbonylamino)phenyl}ethoxy]phenyl)propanoic acid ethyl ester

HRID 987278Notes

Reaction equation

HRID 987278 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1)[CH3:3].Cl[C:29]([O:31][CH3:32])=[O:30]>O1CCCC1>[CH2:2]([O:4][C:5](=[O:27])[C@@H:6]([O:24][CH2:25][CH3:26])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 86595066HCID 86595066, compound

Product 1

HCID 53794173(S)-2-ethoxy-3-(4-[2-{4-(methoxycarbonylamino)phenyl}ethoxy]phenyl)propanoic acid ethyl esterYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (0.55 g; 1.4 mmole) was dissolved in tetrahydrofuran (5 ml) and methyl chloroformate (0.534 g; 5.68 mmole) was added slowly. The reaction mixture was continuously checked with HPLC and after 6 days was all the starting material consumed. Water was added to the mixture, tetrahydrofuran was evaporated and the residue extracted three times with ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated and 0.525 g (90.2%) of (S)-2-ethoxy-3-(4-[2-{4-(methoxycarbonylamino)phenyl}ethoxy]phenyl)propanoic acid ethyl ester was obtained.

Workup

  1. customconsumed
  2. additionWater was added to the mixture, tetrahydrofuran
  3. customwas evaporated
  4. extractionthe residue extracted three times with ethyl acetate
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-be1bb914f58f4bcc86fdb92bc7b53561
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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