Sodium Bicarbonate → 2-(2-Hydroxyethyl)-5-(4-aminobenzenesulfonyl)-1,5-benzothiazepine

HRID 2296756Notes

Reaction equation

HRID 2296756 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[S:5]1.C([O-])(O)=O.[Na+]>Cl.CO>[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[S:5]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 183874282-(2-Hydroxyethyl)-5-(4-acetamidobenzenesulfonyl)-1,5-benzothiazepine

Product 1

HCID 183874372-(2-Hydroxyethyl)-5-(4-aminobenzenesulfonyl)-1,5-benzothiazepineYield 92%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

2-(2-Hydroxyethyl)-5-(4-acetamidobenzenesulfonyl)-1,5-benzothiazepine as prepared in Example 24 was dissolved in a 10% HCl/MeOH (100 ml) solution and stirred at reflux for 2½ hours. The mixture was cooled and a saturated NaHCO3 solution 160 ml) was added. The methanol was removed under reduced pressure and the aqueous mixture extracted with EtOAc (2×80 ml). The combined EtOAc extracts were dried (MgSO4), filtered and evaporated in vacuo to give the desired product as a solid (2.4 g,92%) m.p. 145-148° C. 1H NMR (300 MHz, DMSOd6) 6 7.50( d, J=7 Hz, 1H); 7.41 (d, J=8.6 Hz, 2H); 7.33-7.19 (m, 3H); 6.59 (d, J=8.6 Hz, 2H); 6.05(s, 2H) 4.51 (t, J=5 Hz, 1H); 3.45-3.35 (m, 4H); 2.96 (m, 1H), 2.07(m, 1H); 1.81(m, 1H); 1.49(m, 2H) . m/z (MH+) 365.

Workup

  1. temperatureat reflux for 2½ hours
  2. temperatureThe mixture was cooled
  3. customThe methanol was removed under reduced pressure
  4. extractionthe aqueous mixture extracted with EtOAc (2×80 ml)
  5. dry with materialThe combined EtOAc extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-342fe9e530114c8496b944eef23b3af0
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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