Fmoc-L-hydroxyproline

Light brown solid

FmocHypOH (10.0 g, 28.3 mmol) was suspended in 100 ml 80% MeOH and Cs2C03 (4.6 g, 14.1 mmol) was added. The suspension was stirred at 50C for 30 minutes until complete dissolution. The reaction mixture was concentrated to dryness and resolved in 100 ml DMF. Allylbromide (1 .6 ml, 3.6 g, 29.7 mmol) was added dropwise and the reaction was stirred over night at RT. DMF was distilled off and the residue dissolved in tert-butylmethyl ether. Precipitates were filtered and the clear solution was absorbed on Celite prior column chromatography. The compound was purified on 220 g Silicagel with an n-hexane/ethyl acetate gradient. Yield: 1 1.5 g, 100%FmocHypOH (10.0 g, 28.3 mmol) was suspended in 100 ml 80% MeOH and Cs2003 (4.6 g, 14.1 mmol) was added. The suspension was stirred at 50C for 30 minutes until complete dissolution. The reaction mixture was concentrated to dryness and resolved in 100 ml DMF. Allylbromide (1.6 ml, 3.6 g, 29.7 mmol) was added dropwise and the reaction was stirred over night at RT. DMF was distilled off and the residue dissolved in tert-butylmethyl ether. Precipitates were filtered and the clear solution was absorbed on Celite prior column chromatography. The compound was purified on 220 g Silicagel with an n-hexane/ethyl acetate gradient.Yield: 11.5g, 100%FmocHypOH (10.0 g, 28.3 mmol) was suspended in 100 ml 80% MeOH and CS2CO3 (4.6 g, 14.1 mmol) was added. The suspension was stirred at 50C for 30 minutes until complete dissolution. The reaction mixture was concentrated to dryness and redissolved in 100 ml DMF. Allylbromide (1 .6 ml, 3.6 g, 29.7 mmol) was added dropwise and the reaction was stirred over night at room temperature. DMF was distilled off and the residue dissolved in terf-butyl methyl ether. Precipitates were filtered and the clear solution was absorbed on Celite prior column chromatography. The compound was purified on 220 g Silicagel with n-hexane/ethylacetate gradient. Yield: 1 1 .5 g, 100%FmocHypOH (10.0 g, 28.3 mmol) was suspended in 100 ml 80% MeOH and Cs2003 (4.6 g, 14.1 mmol) was added. The suspension was stirred at 50C for 30 minutes until complete dissolution. The reaction mixture was concentrated to dryness and redissolved in 100 ml DMF. Allylbromide (1.6 ml, 3.6 g, 29.7 mmol) was added dropwise and the reaction was stirred over night at room temperature. DMF was distilled off and the residue dissolved in tert-butylmethyl ether. Precipitates were filtered and the clear solution was absorbed on Celite prior column chromatography. The compound was purified on 220 g silicagel with n-hexane/ethylacetate gradient.Yield: 11.5g, 100%

Molecular Weight:353.4
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:353.12632271
Monoisotopic Mass:353.12632271
Topological Polar Surface Area:87.1
Heavy Atom Count:26
Complexity:530
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes