Pyridine → HCID 67661077, compound

HRID 964715Notes

Reaction equation

HRID 964715 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[N:24]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:23](=[O:30])[C@@H:22]([CH2:31][C:32]([NH2:34])=O)[S:21][C@H:20]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[C:19]=2[CH:45]=1.N1C=CC=CC=1>CCOCC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]2[N:24]([CH2:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C:23](=[O:30])[C@@H:22]([CH2:31][C:32]#[N:34])[S:21][C@H:20]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[C:19]=2[CH:45]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 67661527HCID 67661527, compound

Product 1

HCID 67661077HCID 67661077, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoroacetic anhydride (441 mg, 210 mmol, 296 μL) was added to a solution of trans-7-chloro-5-(naphthalen-1-yl)-1-neopentyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzothiazepine-3-acetamide (98 mg, 210μmol) and pyridine (2.1 mL) at 0° C. After 1.5 h, the reaction mixture was diluted with ether, washed with water (2×) and 0.5 N aqueous hydrochloric acid, dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by flash column chromatography (methylene chloride) to give 88 mg (93%) of the title compound as a white solid.

Workup

  1. washwashed with water (2×) and 0.5 N aqueous hydrochloric acid
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-0446a1c1bcca4cadb809cdc2d7a31e9b
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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