1,1'-Carbonyldiimidazole → HCID 178527060, compound
Reaction equation
OC(C[PH:11]([CH2:13][S:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1)=[O:12])(CC(C)C)C(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=[O:26].O=C1CCC2=CN(C3C=CC=CC=32)CCCCCCN1>C1COCC1>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[S:14][CH2:13][PH:11](=[O:12])[OH:26]Participants
Procedure
A single stereoisomer of 2-(hydroxy) (quinolin-2-ylthiomethyl)phosphinoylmethyl-4-methylpentanoic acid (300 mg, 0.81 mmol) and 1,1'-carbonyldiimidazole (174 mg, 1.0 mmol) were stirred at 0° C. in 6 mL THF for 11/2 hours. (10S)-10-Amino-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraene (270 mg, 0.95 mmol) was added to the solution and the resulting mixture was allowed to warm to room temperature and then stirred for 18 hours. The THF was removed by evaporation and the residue dissolved in 60 mL ethyl acetate. The ethyl acetate was washed with 10 mL H2O, 10 mL brine, dried with MgSO4 and evaporated to yield (10S)-[4-methyl-2-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19) 13(18)14,16-tetraen-10-ylcarbamoyl)pentyl](quinolin-2-ylthiomethyl)phosphinic acid as a yellow oil. Purification was carried out by reverse phase HPLC using a gradient of acetonitrile and 50 mm NH4OAc buffer as the eluents. The more polar stereoisomer was isolated (30 mg) at 41% acetonitrile, and the less polar stereoisomer (10 mg) at 43% acetonitrile. The fractions were lyophilized to off-white powders, MS: 635 (MH+).
Workup
- customThe THF was removed by evaporation
- dissolutionthe residue dissolved in 60 mL ethyl acetate
- washThe ethyl acetate was washed with 10 mL H2O, 10 mL brine
- dry with materialdried with MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-5e3a3d074b1d4546aaac1a6809ecd7d6
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773428
Reaction notes
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