4-Methylmorpholine → H-Gly-Asp(OBzl)-Val-OBzl

HRID 1376687노트

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HRID 1376687 반응식
[NH2:1][C@H:2]([C:14]([NH:16][C@H:17]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.FC(C(O)=O)(F)F.[NH:38](C(OC(C)(C)C)=O)[CH2:39][C:40](ON1C(=O)CCC1=O)=[O:41].CN1CCOCC1>C(OCC)(=O)C>[NH2:38][CH2:39][C:40]([NH:1][C@H:2]([C:14]([NH:16][C@H:17]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:41]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 131720167H-Asp(OBzl)-Val-OBzl.TFA

생성물 1

HCID 131720165H-Gly-Asp(OBzl)-Val-OBzl

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

A solution of 4.2 g. of H-Asp(OBzl)-Val-OBzl.TFA in 50 ml of ethyl acetate is treated in succession with 2.72 g of Boc-Gly-OSu and 0.88 ml of N-methylmorpholine and then stirred at 20° C. for 72 hours. The reaction mixture is partitioned between ethyl acetate and water and the organic phase is washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution. After drying the solution is concentrated. The residue is dissolved in 30 ml of trifluoroacetic acid held at 20° C. for 20 minutes and then concentrated. After crystallization from ethyl acetate/hexane there are obtained 3.5 g of H-Gly-Asp(OBzl)-Val-OBzl, TFA (1:1), m.p. 150°-151° C.

후처리

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. washthe organic phase is washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution
  3. customAfter drying the solution
  4. concentrationis concentrated
  5. dissolutionThe residue is dissolved in 30 ml of trifluoroacetic acid
  6. waitheld at 20° C. for 20 minutes
  7. concentrationconcentrated
  8. customAfter crystallization from ethyl acetate/hexane there

출처 및 근거

ORD 기록
ord-0619bf1890e8441487c3a96f4ce9cd74
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663297

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