Methanol → 2-(2-Hydroxyethyl)-5-(4-acetamidobenzenesulfonyl)-1,5-benzothiazepine

HRID 2296755Notes

Reaction equation

HRID 2296755 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][CH:10]=1.[C:15]([NH:18][C:19]1[CH:28]=[CH:27][C:22]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][CH:20]=1)(=[O:17])[CH3:16].CO>N1C=CC=CC=1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([S:23]([C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 8481N-Acetylsulfanilyl chlorideHCID 183874452-(2-Hydroxyethyl)-1,5-benzothiazepine

Product 1

HCID 183874282-(2-Hydroxyethyl)-5-(4-acetamidobenzenesulfonyl)-1,5-benzothiazepineYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(2-hydroxyethyl)-1,5-benzothiazepine as prepared in Example 2 (3 g, 14.4 mM) in pyridine (30 ml) was slowly added N-acetylsulfanilyl chloride (6.7 g, 28.7 mM). The resulting mixture was stirred at room temperature for 16 hours and the excess pyridine was removed under reduced pressure. The residual semi-solid was diluted with H2O (80 ml) and extracted with CH2Cl2 (2×80 ml). The combined methylene chloride extracts were dried (MgSO4), filtered and evaporated in vacuo to give a crude oil. Flash column chromatography (EM silica gel 60; 2% MeOH in CH2Cl2) gave the desired product as a white solid (2.9 g, 50%). m/z (MH+)407

Workup

  1. customthe excess pyridine was removed under reduced pressure
  2. additionThe residual semi-solid was diluted with H2O (80 ml)
  3. extractionextracted with CH2Cl2 (2×80 ml)
  4. dry with materialThe combined methylene chloride extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude oil

Sources & evidence

ORD record
ord-9e9f207874644e91a407d0c1941372fa
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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