4-Methylmorpholine → Z-Asp(OtBu)-Leu-OBzl

HRID 1417140

반응식

HRID 1417140 반응식
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:39][C@H:40]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:41][CH:42]([CH3:44])[CH3:43]>C1COCC1.C(N(CC)CC)C>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([NH:39][C@H:40]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:41][CH:42]([CH3:44])[CH3:43])=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 6451313Benzyl L-leucinate

생성물 1

HCID 131721133Z-Asp(OtBu)-Leu-OBzl

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

Z-Asp(OtBu)-OH (10.23 g) in THF (50 mL) was added N-methyl-morpholine (3.30 mL) and isobutyl chloroformate (3.90 mL) at -20° C. After 10 min, the reaction mixture was added to the solution of H-Leu-OBzl (11.81 g in 50 mL HCl3) at -20° C., followed by addition of triethylamine (4.18 mL). The resulting mixture was allowed to warm to room temp. After filtering off the salt, the filtrate was concentrated to an oil. The oil was dissolved in 100 mL of ethyl acetate; washed with 0.2N HCl, 5% NaHCO3 and sat. NaCl; dried over Na2SO4. After filtration, the solvent was evaporated to give Z-Asp(OtBu)-Leu-OBzl as an oil of 14.81 g.

후처리

  1. filtrationAfter filtering off the salt
  2. concentrationthe filtrate was concentrated to an oil
  3. dissolutionThe oil was dissolved in 100 mL of ethyl acetate
  4. washwashed with 0.2N HCl, 5% NaHCO3 and sat. NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-ead94c459d5c470abb0a857f00ba5182
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05876945

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