Triethylamine → HCID 131736657, compound
Reaction equation
CS(O[CH2:6][C@H:7]1[CH2:19][N:10]2[C:11]3[CH:12]=[CH:13][C:14]([Br:18])=[CH:15][C:16]=3[CH:17]=[C:9]2[C@H:8]1[N:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:21])(=O)=O.[N-]=[N+]=[N-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:54](CC)CC)C.[C:59]([O:63][C:64]([O:66]C(OC(C)(C)C)=O)=O)([CH3:62])([CH3:61])[CH3:60]>CN(C=O)C.O>[CH2:22]([N:20]([CH3:21])[C@@H:8]1[C:9]2=[CH:17][C:16]3[CH:15]=[C:14]([Br:18])[CH:13]=[CH:12][C:11]=3[N:10]2[CH2:19][C@@H:7]1[CH2:6][NH:54][C:64](=[O:66])[O:63][C:59]([CH3:62])([CH3:61])[CH3:60])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
The crude material from Step 3 was dissolved in DMF (5 mL) and treated with NaN3 (234 mg, 3.6 mmol). The mixture was heated at 80° C. for 2 h. To the mixture was added H2O (1 mL) and triphenylphosphine (524 mg, 2 mmol). The mixture stirred at 80° C. for 1 h. After cooling the mixture to room temperature, triethylamine (0.5 mL, 3.6 mmol) and di-tert-butyldicarbonate (436 mg, 2.0 mmol) were added sequentially. The mixture was stirred at room temperature for 1 h. The mixture was concentrated and chromatographed on silica gel (0-8% MeOH in CH2Cl2) to afford the product (300 mg, 35%).
Workup
- temperatureAfter cooling the mixture to room temperature
- stirringThe mixture was stirred at room temperature for 1 h
- concentrationThe mixture was concentrated
- customchromatographed on silica gel (0-8% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-c39bee68940a49808ca7a3fad1ae913e
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409905B2
Reaction notes
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