4-Methylmorpholine → Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

HRID 2356036노트

반응식

HRID 2356036 반응식
[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[CH:24]1[C:23]2[CH:22]([CH2:21][O:20][C:18]([NH:1][C@@H:2]([CH2:15][OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:19])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

생성물 1

HCID 11655404Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-5 °C

실험 절차

A solution of Fmoc-D-Lys(BOC)-OH (2.102 g, 4.5 mmol) in DME (5 mL) at −15° C. was treated successively with N-methylmorpholine (0.56 mL, 5.0 mmol) and isobutyl chloroformate (0.7 mL, 5 mmol), stirred for 2 minutes, and filtered. The filter cake was washed with DME (3×5 mL) and the combined filtrate and washings were cooled to −5° C. and treated with NaBH4 (0.3 g, 7.5 mmol) in water (5 mL) and additional water (250 mL) immediately afterwards. The mixture was stirred for 15 minutes and filtered. The filter cake was washed with water and dried to provide the desired product. MS (APCI) m/e 455 (M+H)+.

후처리

  1. filtrationfiltered
  2. washThe filter cake was washed with DME (3×5 mL)
  3. stirringThe mixture was stirred for 15 minutes
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried

출처 및 근거

ORD 기록
ord-290cb8c61e834c27bf0520d9dcd562c0
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754886B2

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