Toluene → HCID 178446186, compound

HRID 964716Notes

Reaction equation

HRID 964716 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]#[N:20])[S:8][C@H:7]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:31]=1.C[Sn]([N:36]=[N+:37]=[N-:38])(C)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]3[NH:38][N:37]=[N:36][N:20]=3)[S:8][C@H:7]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 5104973Azido(trimethyl)stannaneHCID 67661077HCID 67661077, compound

Product 1

HCID 178446186HCID 178446186, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A heterogeneous mixture of trans-7-chloro-5-(naphthalen-1-yl)-1-neopentyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzothiazepine-3-acetonitrile (75 mg, 167 μmol), trimethyltin azide (70 mg, 334 μmol) and toluene (2 mL) was heated at reflux for 18 hours. Reaction mixture concentrated under reduced pressure and purified by flash column chromatography (80:15:1 chloroform/methanol/ammonium hydroxide) to yield a clear oil which was taken up in ethyl acetate, washed with 0.5 N hydrochloric acid, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 58.5 mg (71 %) of the title compound as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customReaction mixture
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (80:15:1 chloroform/methanol/ammonium hydroxide)
  6. customto yield a clear oil which
  7. washwashed with 0.5 N hydrochloric acid
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4e9aa5874034ee79ebb14697bf0e299
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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