Triphenylphosphine → tert-butyl 2-{4-[(1S)-1-benzyl-2-(benzyloxy)-2-oxoethoxy]benzoyl}hydrazinecarboxylate

HRID 642165Notes

Reaction equation

[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])=[CH:4][CH:3]=1.O[C@H:20]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N(C(OCC)=O)=NC(OCC)=O>[CH2:31]([C@H:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:7])=[CH:17][CH:18]=1)[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of tert-butyl 2(4-hydroxybenzoyl)hydrazinecarboxylate (200 mg, 0.79 mmol) and benzyl (R)-(+)-2-hydroxy-3-phenylpropionate (Aldrich) (270 μL, 1.19 mmol) were added triphenylphosphine polymer bound (Fluka, 3 mmol/g, 400 mg) and diethyl azodicarboxylate (190 μL) at 0° C. The resulting mixture was allowed to stir for 2 hr at 0° C. After filtration and rinsing the resin with DCM, the filtrate was evaporated off under vacuo to give a brown residue. Purification by flash chromatography (SiO2, AcOEt/chexanes (2/3)) gave the title compound as a white powder (216 mg, 56%) in 99.4% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

customat 0° C
filtrationAfter filtration
washrinsing the resin with DCM
customthe filtrate was evaporated off under vacuo
customto give a brown residue
customPurification by flash chromatography (SiO2, AcOEt/chexanes (2/3))

Sources & evidence

ORD record: ord-0ade082031ff405dbdfc1e9beb45b468
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696231B2

Reaction notes

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