Triethylamine → HCID 86594583, compound
Reaction equation
[Br:1][C:2]1[C:3]([CH3:16])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([OH:15])=O)[CH2:9][CH:10]([CH3:12])[CH3:11].C1CN([P+](O[N:34]2N=[N:41][C:36]3C=CC=C[C:35]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C>CN(C=O)C.CCOCC>[Br:1][C:2]1[C:3]([CH3:16])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([NH:41][CH2:36][C:35]#[N:34])=[O:15])[CH2:9][CH:10]([CH3:11])[CH3:12]Participants
Procedure
To an ice cold solution of N-(4-bromo-3-methylisothiazol-5-yl)-L-leucine (9.83 g, 32 mmol), PyBOP (18.6 g, 35.7 mmol) and 2-aminoacetonitrile hydrochloride (6.5 g, 70.3 mmol) in DMF (250 mL) was slowly added over 5 min triethylamine (15.6 mL, 112 mmol). The resulting suspension was stirred at room temperature for 18 h. The reaction mixture was partitioned between EtOAc and half-saturated NaHCO3. The organic layer was washed once with water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc in hexane to give a colorless syrup. This syrup was disolved in Et2O, washed once with 3% HCl and once with diluted NaHCO3, dried over Na2SO4 and concentrated in vacuo to give N2-(4-bromo-3-methylisothiazol-5-yl)-N1-(cyanomethyl)-L-leucinamide as a white foam.
Workup
- customThe reaction mixture was partitioned between EtOAc and half-saturated NaHCO3
- washThe organic layer was washed once with water
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
- customto give a colorless syrup
- washwashed once with 3% HCl and once with diluted NaHCO3
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4b945a56da8e4f789cfdacf2497604ce
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07012075B2
Reaction notes
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