Tributyltin azide → HCID 59432391, compound

HRID 507095Notes

Reaction equation

HRID 507095 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)[C:23]#[N:24])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:40]([Sn](CCCC)(CCCC)CCCC)=[N+:41]=[N-:42]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:25][C:26]2[CH:27]=[C:28]([C:36]([F:38])([F:39])[F:37])[CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=2)[C:23]2[N:40]=[N:41][NH:42][N:24]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 59432365HCID 59432365, compound

Product 1

HCID 59432391HCID 59432391, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-9-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (1.61 mmol) in toluene (10 mL), add azidotributyltin (3.22 mmol) and heat to 100° C. After stirring for 12 h, cool the reaction to room temperature and quench with methanol (1 mL). Dilute the reaction mixture with ethyl acetate (100 mL) and wash with aqueous sodium fluoride (50 mL) and brine (50 mL). Dry the organic portion over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with methanol/dichloromethane (1-5%) to afford the title compound as a colorless foam. MS (ES+): 597.3 (M−H).

Workup

  1. temperaturecool
  2. customthe reaction to room temperature
  3. customquench with methanol (1 mL)
  4. additionDilute the reaction mixture with ethyl acetate (100 mL)
  5. washwash with aqueous sodium fluoride (50 mL) and brine (50 mL)
  6. dry with materialDry the organic portion over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under vacuum
  9. washChromatograph the product over silica gel, eluting with methanol/dichloromethane (1-5%)

Sources & evidence

ORD record
ord-3de5789495454b1a977326d00149b396
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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