Triethylamine → HCID 86758122, compound
Reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:4].C(N(CC)CC)C.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:32][C@@H:33]1[O:35][CH2:34]1)(=O)=O>CN(C=O)C>[CH2:19]([N:10]1[C:9]2[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][CH2:32][C@H:33]3[CH2:34][O:35]3)=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-amino-N-(9-ethyl-9H-carbazol-3-yl)-acetamide (6.1 g, 23 mmol) and triethylamine (6.3 mL, 45 mmol) in DMF (50 mL) was added a solution of (R)-(−)-glycidyl nosylate (5.9 g, 23 mmol) in DMF (20 mL). The resultant solution was stirred two days under nitrogen to form (S)-N-(9-Ethyl-9H-carbazol-3-yl)-2-(oxiranylmethyl-amino)-acetamide, which was then directly treated with diethyl amine (23 mL, 227 mmol) and methanol (100 mL). The mixture was stirred an additional two days, and then concentrated under reduced pressure to remove the methanol. The concentrated reaction was diluted with ethyl acetate (1 L) and washed with saturated aqueous Na2CO3 (1 L), water (2×500 mL), and then brine (250 mL). The organic solution was then dried (Na2SO4), concentrated under reduced pressure, and flash chromatographed (10:3:1 to 7:3:1 hexanes/diethylamine/acetonitrile) to give the title compound (4.4 g, 49%) as a brown oil which was converted to the dihydrochloride salt (methanol, ethereal HCl). The salt was then re-pulped from refluxing 2:1 ether/methanol to afford the dihydrochloride salt of the title compound as a colorless solid (3.5 g, 33%). MS m/z @ 397 (M+1).
Sources & evidence
- ORD record
- ord-3af451696b18409291c5c41b6427e309
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06399631B1
Reaction notes
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