Tributyltin azide → HCID 59432476, compound

HRID 507058Notes

Reaction equation

HRID 507058 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C:16]#[N:17])[C:10]2[CH:33]=[C:34]([CH2:41][CH3:42])[C:35]([C:37]([F:40])([F:39])[F:38])=[CH:36][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:43]([Sn](CCCC)(CCCC)CCCC)=[N+:44]=[N-:45]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([CH2:18][C:19]2[CH:20]=[C:21]([C:29]([F:31])([F:32])[F:30])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=2)[C:16]2[N:43]=[N:44][NH:45][N:17]=2)[C:10]2[CH:33]=[C:34]([CH2:41][CH3:42])[C:35]([C:37]([F:40])([F:38])[F:39])=[CH:36][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4984872Tributyltin azideHCID 59432307HCID 59432307, compound

Product 1

HCID 59432476HCID 59432476, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat a mixture of (S)-5-[(3,5-bistrifluoromethylbenzyl)cyanoamino]-7-ethyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid tert-butyl ester (0.510 g, 0.837 mmol), azidotributyltin (0.344 mL, 1.26 mmol) in anhydrous toluene (20 mL) at 100° C. under nitrogen for 16 h. Dilute the cooled mixture with ethyl acetate (50 mL) and wash with aqueous NaF (50 mL) and brine (50 mL). Dry over anhydrous sodium sulfate. Filter and remove the solvent under reduced pressure. Purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (0-60%), to provide the title compound (0.432 g, 79%), MS (ES+): 653 (M+H).

Workup

  1. temperatureHeat
  2. washwash with aqueous NaF (50 mL) and brine (50 mL)
  3. dry with materialDry over anhydrous sodium sulfate
  4. filtrationFilter
  5. customremove the solvent under reduced pressure
  6. customPurify the residue by column chromatography on silica gel
  7. washeluting with ethyl acetate/hexanes (0-60%)

Sources & evidence

ORD record
ord-8ab84ebc781448e3a2dee3a6a2084cb2
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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