Sodium Carbonate → HCID 70081162, compound

HRID 1289489Notes

Reaction equation

HRID 1289489 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:9][C:10]([C@H:12]1[CH2:17][C:16]([CH3:18])=[CH:15][CH2:14][N:13]1[C:19](=[O:50])[C@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([C:48]#[N:49])[CH:43]=1)[NH:21][S:22]([C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][N:31](C(=O)C(F)(F)F)[CH2:32]2)=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[O:11])[CH3:8]>O.C(O)C>[CH2:7]([O:9][C:10]([C@H:12]1[CH2:17][C:16]([CH3:18])=[CH:15][CH2:14][N:13]1[C:19](=[O:50])[C@H:20]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([C:48]#[N:49])[CH:43]=1)[NH:21][S:22]([C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][NH:31][CH2:32]2)=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[O:11])[CH3:8]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 86752537HCID 86752537, compound

Product 1

HCID 70081162HCID 70081162, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium carbonate (2.83 g, 26.7 mmol) in water (20 ml) was added to a stirred solution of 4-methyl-1-[N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanyl]-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid ethyl ester (Preparation 36; 3.38 g, 5.34 mmol) in ethanol (20 ml) and the resulting suspension stirred for 20 hours. The bulk of the ethanol was removed under reduced pressure, the residual mixture diluted with water and extraction with ethyl acetate effected. The organic extract was washed with water, then saturated brine, dried (MgSO4) and evaporated under reduced pressure to afford the title compound (2.29 g) as a foam. Rf 0.42 (SS 9). [α]D25 +14° (c=0.1, CH3OH). Found: C,61.60; H,6.06; N,10.10. C28H32N4O5S; 0.50 H2O requires C,61.63; H,6.09; N,10.26%.

Workup

  1. customThe bulk of the ethanol was removed under reduced pressure
  2. additionthe residual mixture diluted with water and extraction with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialsaturated brine, dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba24a2b874da4d37992d0f2101dac64d
Source dataset
uspto-grants-1998_05
Patent number
US05750520

Reaction notes

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