Triphenylphosphine → HCID 58646553, compound

HRID 1353263Notes

Reaction equation

[C:1]([O:5][C:6](=[O:10])[C@H:7]([OH:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:11]([O:13][C:14](=[O:27])[C@@H:15]([O:24][CH2:25][CH3:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1)[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:11]([O:13][C:14](=[O:27])[C@@H:15]([O:24][CH2:25][CH3:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:9][C@H:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:10])[CH3:8])=[CH:19][CH:18]=1)[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(R)-hydroxypropionic acid tert-butyl ester (1.23 g, 8.44 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (2.01 g, 8.44 mmol) in THF (100 ml) was added the triphenyl phosphine (2.21 g, 8.44 mmol). The mixture was cooled to 0° C. and added the DIAD (diisopropyl azodicarboxylate) (1.70 g, 8.44 mmol) dropwise over 5 minutes. The reaction mixture was stirred for 18 hours while warmed to room temperature. The reaction was quenched with water (2 ml) and concentrated to a residue, purified by silica gel chromatography with 20% EtOAc/Hexanes to afford product (0.99 g, 32%) and recovered starting material ((S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester, 0.85 g).

Workup

temperaturewhile warmed to room temperature
customThe reaction was quenched with water (2 ml)
concentrationconcentrated to a residue
custompurified by silica gel chromatography with 20% EtOAc/Hexanes

Sources & evidence

ORD record: ord-6c332589117f450ba48f5350b14a6ada
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220880B2

Reaction notes

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