Formic Acid → HCID 86740632, compound

HRID 1285357Notes

Reaction equation

HRID 1285357 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[CH:28]([OH:30])=[O:29].[C:31]([O:34]C(=O)C)(=[O:33])C>N1C=CC=CC=1>[C:31]([OH:34])(=[O:33])[C:28]([OH:30])=[O:29].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][CH:28]=[O:29])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11004065HCID 11004065, compound

Product 1

HCID 86740632HCID 86740632, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.8 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 9 ml of formic acid, 3 ml of acetic anhydride and one ml of pyridine is stirred at room temperature for 3 days. The reaction mixture is evaporated under reduced pressure to remove solvent. The residue is converted into its oxalate and recrystallized from a mixture of ethanol and ether. 0.725 g of (+)-cis-2-(4-methoxyphenyl)-3-formyloxy-5-[2-(dimethylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one oxalate is obtained.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove solvent
  3. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-3e995d81282942b5a47802457cadb9fd
Source dataset
uspto-grants-1986_01
Patent number
US04567175

Reaction notes

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