Triphenylphosphine → HCID 131718527, compound

HRID 1728373Notes

Reaction equation

[CH3:1][C:2]([CH3:27])([O:4][C:5]([C@H:7]([NH:11][C@H:12]([C:17]([O: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)=[O:6])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:47]=[C:48]1[C:56]2[CH:55]=[C:54]3[CH:57]=[CH:58][CH:59]=[CH:60][C:53]3=[CH:52][C:51]=2[C:50](=[O:61])[NH:49]1>O1CCCC1>[CH3:3][C:2]([CH3:1])([O:4][C:5]([C@H:7]([NH:11][C@H:12]([C:17]([O: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:49]1[C:50](=[O:61])[C:51]2[CH:52]=[C:53]3[CH:60]=[CH:59][CH:58]=[CH:57][C:54]3=[CH:55][C:56]=2[C:48]1=[O:47])=[O:6])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

2.5 g of N-[(R)-1-[(1,1-dimethylethoxy)carbonyl]-3-hydroxypropyl]-L-leucine, phenylmethyl ester, prepared as in Example J, 1.85 g triphenylphosphine, and 1.4 g 1,3-dihydro-1,3-dioxo-2H-Benz[f]isoindole in 100 mL dry tetrahydrofuran was cooled to 0° C. and treated with 1.1 mL diethylazidodicarboxylate. The resulting mixture was allowed to warm up to 23° C. over 24 h and the solvent removed by evaporation. The residue was purified by silica chromatography using methylene chloride as eluent to give a light yellow solid. Trituration with 20 mL methanol and filtration gave the title compound as a white solid which crystallized from methanol; 1.9 g.

Workup

temperatureto warm up to 23° C. over 24 h
customthe solvent removed by evaporation
customThe residue was purified by silica chromatography
customto give a light yellow solid
filtrationTrituration with 20 mL methanol and filtration

Sources & evidence

ORD record: ord-9dc3886a68044e2d83982ba6091391df
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326760

Reaction notes

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