Acetic Acid → HCID 70272651, compound
Reaction equation
[N+](=[CH2:3])=[N-].[CH:4]([C:7]([N:17]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:18]([C@H:20]([NH:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:19])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8](=[O:10])[NH2:9])([CH3:6])[CH3:5].C(O)(=O)C>C(OCC)C.O1CCCC1>[CH3:3][O:24][C:23](=[O:25])[CH2:22][CH2:21][C@H:20]([C:18](=[O:19])[N:17]([C:7]([CH:4]([CH3:6])[CH3:5])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:8](=[O:10])[NH2:9])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[NH:26][C:27]([NH:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of diazomethane in diethyl ether (generated from N-methylnitroso urea, 623 mg and 40% aqueous potassium hydroxide, 2 mL) was added dropwise to a solution of Example 4 (11.2 mg, 0.0217 mmol) in tetrahydrofuran (2 mL) until a yellow color persisted. Acetic acid was added until yellow color disappeared and the solvents were removed in vacuo. RP-HPLC (45% to 64%, 30 min) gave the titled product (10.3 mg) as a white lyophile. (45% to 64%, 30 min) Tr =13.07 min. 1H NMR (300 MHz, CDCl3) d 1.0 (2×d, J=7.0 Hz, 6H), 1.90 (m, 1H), 2.07 (m, 1H), 2.20 (m, 1H), 2.41 (m, 1H), 3.40 (d, J=16.6 Hz, 1H), 4.21 (s, 3H), 4.36 (d, J=16.6.0 Hz, 1H), 4.70 (m, 1H), 5.20 (sept, J=6.0 Hz, 1H), 6.57 (d, J=7.0 Hz, 1H), 6.88 (m, 4H), 7.10 (m, 4H), 7.21 (br, 2H), 7.38 (m, 4H), 7.59 (d, J=7.0 Hz, 2H), 8.30 (s, 1H). C31H36N4O6 requires m/z 560.6502; found 560.6541.
Workup
- customthe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-1dd6ecd368f0495f8f7237ae9a09d3c6
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05889182
Reaction notes
Loading…