반응 #336810

반응 방정식

1-ethyl-3-(3-dimethylamino-propyl)carbodiimide

6-aminohexanoic acid methyl ester hydrochloride salt

N-Cbz-β-alanine

Et3N

→

desired product ( 35 )

수율 91.3%

6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl ester

수율 91.3%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The compound 35 was prepared
2. 2
   기타Recrystallization of the crude product
3. 3
   workup.ADDITIONfrom a mixture of MeOH and H2O (10:1 ratio)

실험 절차

The compound 35 was prepared using General Procedure B with 6-aminohexanoic acid methyl ester hydrochloride salt (3.0 g, 16.5 mmol), N-Cbz-β-alanine (3.68 g, 16.5 mmol), 1-hydrobenzotriazole (HOBt) (2.68 g, 19.8 mmol), 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide (EDC) (3.80 g, 19.8 mmol) and Et3N (5.52 mL, 39.6 mmol) in CH2Cl2, (100 mL). Recrystallization of the crude product from a mixture of MeOH and H2O (10:1 ratio) afforded 5.28 g (91%) of the desired product (35) as a white solid. 1H NMR (CDCl3): 7.32 (m, 5H, ArH), 5.82 (s, 1H, NH), 5.54 (s, 1H, NH), 5.07 (s, 2H, OCH2Ar), 3.64 (s, 3H, OCH3), 3.45 (dt, J=6.1, 12.0 Hz, 2H, CH2NHCO), 3.21 (dt, J=6.4, 12.8 Hz, 2H, CH2NHCO), 2.38 (dt, J=6.1, 6.8 Hz, 2H, CH2CO), 2.29 (t, J=7.2 Hz, 2H, CH2CO), 1.61 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.33 (m, 2H, CH2).

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