Phenol → methyl (S)-2-tritylamino-3-phenoxypropionate

HRID 278036Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]([NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][OH:7])=[O:4].[C:28]1(O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:9]([NH:8][C@@H:5]([CH2:6][O:7][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([O:2][CH3:1])=[O:4])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.8 g of trt-Ser-OMe (Bachem), 0.75 of phenol, and 2.25 g of triphenylphosphine were dissolved together in 60 ml of THF, absolute, and treated dropwise with 1.49 g of diethyl azodicarboxylate at 0° C. in the course of 30 min. The reaction mixture was stirred at 0° C. for 30 min and warmed to RT (about 1 h). For working-up, the solvent was removed under reduced pressure and the crude product was purified by chromatography on silica gel (heptane/ethyl acetate=1.5/1). The methyl (S)-2-tritylamino-3-phenoxypropionate thus obtained crystallized slowly in long needles, and was heated under reflux for 1 h in 5 M HCl to remove the protective groups. The reaction solution was evaporated to dryness under reduced pressure by coevaporating a number of times with toluene and the residue was recrystallized from a little tert-butanol.

Workup

temperaturewarmed to RT (about 1 h)
customthe solvent was removed under reduced pressure
customthe crude product was purified by chromatography on silica gel (heptane/ethyl acetate=1.5/1)

Sources & evidence

ORD record: ord-6404e54782ea43ceb2d66f854a11f266
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358978B1

Reaction notes

Loading…