Acetic Acid → HCID 178496735, compound

To a solution of Boc-Thr(Me)-OH (113 mg, 0.48 mmol) in N,N-dimethylformamide (3.0 mL) was added HATU (225 mg, 0.592 mmol). The mixture was stirred for 30 minutes and then 4-cyclopentylbenzene-1,2-diamine (Compound 84, 118 mg, 0.669 mmol) was added. After stirring for 2 days, the solution was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. To the resulting residue was added acetic acid (3 mL, 50 mmol) and the mixture allowed to stir for 2 days. The reaction mixture was then concentrated in vacuo and purified by silica gel column chromatography eluting with 0-100% ethyl acetate in hexanes. The resulting brown oil was dissolved in methylene chloride (5 mL) and treated with trifluoroacetic acid (0.5 mL, 6 mmol). After stirring for 3 hours, the reaction mixture was concentrated in vacuo, redissolved in methylene chloride, and washed with saturated aqueous sodium hydrogen carbonate solution.

1. stirringAfter stirring for 2 days
2. washwashed with water and brine
3. dry with materialdried over anhydrous magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. stirringto stir for 2 days
7. concentrationThe reaction mixture was then concentrated in vacuo
8. custompurified by silica gel column chromatography
9. washeluting with 0-100% ethyl acetate in hexanes
10. dissolutionThe resulting brown oil was dissolved in methylene chloride (5 mL)
11. stirringAfter stirring for 3 hours
12. concentrationthe reaction mixture was concentrated in vacuo
13. dissolutionredissolved in methylene chloride
14. washwashed with saturated aqueous sodium hydrogen carbonate solution

ORD record

ord-6ff42eb02b354e3d9a28a1f0e13abe7d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927587B2