Triphenylphosphine → HCID 18653508, compound

HRID 1728390Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6](=[O:27])[C@H:7]([NH:11][C@H:12]([C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9]O)([CH3:4])[CH3:3].[Br:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:38])[NH:33][C:32]2=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C=O)C>[CH3:1][C:2]([O:5][C:6](=[O:27])[C@H:7]([NH:11][C@H:12]([C:17]([NH:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:8][CH2:9][N:33]1[C:32](=[O:39])[C:31]2[C:35](=[CH:36][CH:37]=[C:29]([Br:28])[CH:30]=2)[C:34]1=[O:38])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

325 mg of 2-(R)-[1-(S)-(benzylamino)carbonyl-3-methyl-butylamino]-4-hydroxy-butanoic acid-1,1-dimethylethyl ester, prepared as described for Example N, was added to 10 mL DMF, followed by 226 mg 5-bromo-1,3-dihydro-1,3-dioxo-2H-isoindole. 231 mg of triphenylphosphine was added and the mixture was cooled to 0° C. 0.14 mL diethyl azodicarboxylate was added and the mixture was warmed to RT with stirring for 16 h. The solvents were removed by evaporation and the resulting residue was purified by reverse phase H.P.L.C. to give the title compound; 53 mg.

Workup

temperaturethe mixture was warmed to RT
customThe solvents were removed by evaporation
customthe resulting residue was purified by reverse phase H.P.L.C

Sources & evidence

ORD record: ord-25023bfb0da34867a1c0f956a9d1ec93
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326760

Reaction notes

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