Sodium Carbonate → N-(1,2,3,4-Tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

HRID 343323Notes

Reaction equation

HRID 343323 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:9][C:10](=[O:41])[C@H:11]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=1)[NH:12][S:13]([C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][N:22](C(=O)C(F)(F)F)[CH2:23]2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:8]>O.C(O)C>[CH2:7]([O:9][C:10](=[O:41])[C@H:11]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=1)[NH:12][S:13]([C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][NH:22][CH2:23]2)=[CH:18][CH:17]=1)(=[O:14])=[O:15])[CH3:8]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54332895N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

Product 1

HCID 54386742N-(1,2,3,4-Tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl esterYield 68.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium carbonate (11.5 g, 108.5 mmol) in water (115 ml) was added to a stirred solution of N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester (Preparation 21; 11.5 g, 22.6 mmol) in ethanol (115 ml) and the resulting mixture stirred for 3 hours at room temperature. The bulk of the ethanol was then removed under reduced pressure, water added and the resulting suspension extracted with dichloromethane. The organic extract was washed with saturated brine, dried (MgSO4) and evaporated under reduced pressure, then the residue dissolved in the minimum volume of dichloromethane. Dilution of this solution with ethanol, followed by concentration and overnight standing of the mixture, provided the title compound as a white solid (6.4 g), after filtration and washing with ether. Rf 0.26 (SS 6). m/e 414 (M+H)+.

Workup

  1. customThe bulk of the ethanol was then removed under reduced pressure, water
  2. additionadded
  3. extractionthe resulting suspension extracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. dissolutionthe residue dissolved in the minimum volume of dichloromethane
  9. concentrationDilution of this solution with ethanol, followed by concentration and overnight

Sources & evidence

ORD record
ord-3c01df0bbd594654a9ed0ae3908e9deb
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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