Triphenylphosphine → HCID 14372051, compound

HRID 1382695Notes

Reaction equation

[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:8][NH:9][C:10](=O)[C@H:11]([CH2:20][OH:21])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]1([C:7](=[N:8][N:9]2[CH2:10][C@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:20]2=[O:21])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 7.9 ml (0.05 mol) of diethyl azidodicarboxylate in 50 ml of tetrahydrofuran was added to a stirred solution of 9.6 g, (0.05 mol) of N-(t-butyloxycarbonyl)-L-serine-2-(diphenylmethylene)hydrazide and 9.6 g, (0.05 mol) of triphenylphosphine in 250 ml of tetrahydrofuran. The mixture was stirred and heated at 55° C. for 6 hours. The resulting solution was evaporated to dryness in vacuo. The residue was dissolved in 50 ml of ethyl acetate and chilled. The crystalline precipitate was removed by filtration and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate-hexane (1:1) as the eluent to afford 12.0 g (66%) of the desired product; mp 167°-170° C.; IR (KBr) 1775 cm-1 (C=O); NMR (CDCL3) δ1.38 (s, 9H, (CH3)3C), 2.85 (dd, 1H, J=3 and 6 Hz, 4βH), 3.25 (t, 1H, J=6 and 6 Hz, 4αH), 4.70 (m, 1H, 3αH), 5.25 (d, 1H, NH), 7.40 (m, 10H, aromatic protons).

Workup

customThe resulting solution was evaporated to dryness in vacuo
dissolutionThe residue was dissolved in 50 ml of ethyl acetate
temperaturechilled
customThe crystalline precipitate was removed by filtration
customthe filtrate was evaporated to dryness
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-5d233f62f8e54e5f9bce02204e51e593
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808579

Reaction notes

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