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4-Methylmorpholine → Boc-Asp(OBzl)-Val-OBzl

HRID 1376686
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HRID 1376686 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:21]([OH:23])=O)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])[CH3:3].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:39][C@H:40]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH:41]([CH3:43])[CH3:42].S(C1C=CC(C)=CC=1)([O-])(=O)=O>CN(C=O)C>[NH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:9]([C:21]([NH:39][C@H:40]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:23])[CH2:10][C:11](=[O:12])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
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참가 물질

7

반응물 5

HCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 85570p-ToluenesulfonateHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 6950584benzyl (2S)-2-amino-3-methylbutanoate

생성물 1

HCID 131720166Boc-Asp(OBzl)-Val-OBzl
수율 103.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
-15 °C

실험 절차

A solution, cooled to -20° C., of 32.3 g of Boc-Asp-(OBzl)-OH in 150 ml of DMF is treated with 11 ml of N-methylmorpholine and 13.07 ml of isobutyl chloroformate. The suspension obtained is stirred at -15° C. and treated with a suspension, cooled to -20° C., of 37.95 g of H-Val-OBzl.tosylate and 11 ml of N-methylmorpholine in 150 ml of DMF. The reaction mixture is stirred at below -10° C. for 10 minutes and at room temperature for 2 hours, filtered and the filtrate is concentrated. The residue is dissolved in ethyl acetate and washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution and dried. The organic phase is concentrated. 52.9 g of Boc-Asp(OBzl)-Val-OBzl are obtained. 10.24 g thereof are dissolved in 30 ml of TFA and then concentrated. The residue, is crystallized from ethyl acetate/hexane. There are obtained 8.3 g of H-Asp- (OBzl)-Val-OBzl.TFA (1:1),.m.p. 147°-148° C.

후처리

  1. customThe suspension obtained
  2. additiontreated with a suspension
  3. stirringThe reaction mixture is stirred at below -10° C. for 10 minutes and at room temperature for 2 hours
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution
  8. customdried
  9. concentrationThe organic phase is concentrated

출처 및 근거

ORD 기록
ord-d1950b753ee047d683003f7c40cb35aa
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05663297

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