반응 #84615

ord-6bdca58dc5264f65ac6e03fd1a1b29f4

반응 방정식

CC(C)(C)OC(=O)CN(CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)Cc1ccccn1
PAMA-K
CC(C)(C)OC(=O)CN(CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)Cc1ccccn1
(S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(pyridin-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid
C1CCNCC1
piperidine
→
CC(C)(C)OC(=O)CN(CCCC[C@H](N)C(=O)O)Cc1ccccn1
(S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid
수율 70.0%

반응물

CC(C)(C)OC(=O)CN(CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)Cc1ccccn1
PAMA-K
CC(C)(C)OC(=O)CN(CCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)Cc1ccccn1
(S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(pyridin-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid
C1CCNCC1
piperidine

시약

없음

용매

CN(C)C=O
DMF

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Solvent was evaporated under reduced pressure
  2. 2
    기타to give a residue, which
  3. 3
    기타was purified by Amberchrom (CG-161C)
  4. 4
    세척eluting with MeOH/H2O

실험 절차

A solution of PAMA-K (0.600 g, 1.047 mmol) and piperidine (1.0 mL) in DMF (5.0 mL) was stirred at room temperature for 3 hrs. Solvent was evaporated under reduced pressure to give a residue, which was purified by Amberchrom (CG-161C) eluting with MeOH/H2O to give (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid (0.256 g, 70%). MS (ESI), 352 (M+H)+.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09433594B2uspto-grants-2016_09