반응 #155404

반응 방정식

N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester

imidazole

TBSCl

HCl

→

desired acid

수율 87.1%

N-Boc-1(R)-amino-2(S)-tert-butyldimethylsilyloxy-cyclopentane-4(S)-carboxylic acid

수율 87.1%

용매

DCM

isopropanol

chloroform

NaOH

반응 조건

후처리

1. 1
   온도by heating at 40° C. for 1 hour
2. 2
   온도The reaction mixture was cooled to room temperature
3. 3
   기타was quenched with H2O (3 mL)
4. 4
   기타The organic layer was separated
5. 5
   농축was concentrated to dryness
6. 6
   기타to yield a residue, which
7. 7
   온도The reaction was cooled to 0° C.
8. 8
   기타the organic layer was separated
9. 9
   건조dried over Na2SO4
10. 10
    농축concentrated to dryness

실험 절차

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

출처