Water → (2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanamido]-3-hydroxypropanoic acid

BOC-L-Ala (567 mg, 2 mMol) and HOBT.H2O (505 mg, 3.3 mMol) were dissolved in 5 ml CH2Cl2 and 5 ml DMF, then treated with 1,3-dicyclohexylcarbodiimide (DCC, 680 mg, 3.3 mMol). The resulting solution was stirred at RT for one hour, then treated dropwise with a solution that contained 421 mg (3.3 mMol) of serinol hydrochloride (Aldrich) and 333 mg (3.3 mMol) of N-methylmorpholine in 5 ml of DMF. The reaction mixture was stirred at RT for 20 hours, then treated with 0.5 ml of glacial acetic acid and stirred for another hour. The solid reaction by-products were removed by filtration and washed with 20 ml CH2Cl2. The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum. The oily residue was taken up in 50 ml of H2O, cooled at 4° C. for several hours, then filtered. The filtrate was concentrated to dryness on the rotary evaporator, then further dried under high vacuum to yield the crude product as a yellow oil.

1. additiontreated dropwise with a solution that
2. stirringThe reaction mixture was stirred at RT for 20 hours
3. stirringstirred for another hour
4. customThe solid reaction by-products
5. customwere removed by filtration
6. washwashed with 20 ml CH2Cl2
7. concentrationThe combined filtrate and washings was concentrated to dryness on the rotary evaporator
8. customthen further dried under high vacuum
9. temperaturecooled at 4° C. for several hours
10. filtrationfiltered
11. concentrationThe filtrate was concentrated to dryness on the rotary evaporator
12. customfurther dried under high vacuum

ORD 기록

ord-d0ab0eaea394488cacd92d78b1a36cb0

출처 데이터셋

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05416070