4-Methylmorpholine → Benzyl (tert-butoxycarbonyl)glycylglycinate

HRID 1086785

반응식

HRID 1086785 반응식
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CCN=C=NCCCN(C)C.[NH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].S(C1C=CC(C)=CC=1)([O-])(=O)=O.CN1CCOCC1>C(Cl)(Cl)Cl.C(#N)C>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:5]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 85570p-ToluenesulfonateHCID 409140Benzyl glycinate

생성물 1

HCID 3244524Benzyl (tert-butoxycarbonyl)glycylglycinate수율 93.7%

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 6342Acetonitrile용매

반응 조건

온도
-15 °C

실험 절차

Boc-Gly-OH (17.52 g, 0.1 mole) in a mixture of CHCl3 (50 ml) and acetonitrile (50 ml) was cooled to -15° C. and EDCI (19.17 g, 0.1 mole) was added and stirred for 20 minutes. To this, a pre-cooled solution of H-Gly-OBzl.tosylate (37.1 g, 0.11 mole), NMM (12.09 ml, 0.11 mole) in CHCl3 (100 ml) was added and stirred overnight at room temperature. After removing the solvent, the residue was taken in CHCl3 and extracted with acid and base. Chloroform was removed under reduced pressure, triturated with pet. ether, filtered, washed with pet. ether and dried to obtain 30.2 g of I (yield: 93.7%), m.p. 82°-83° C. Rf2, 0.52; Rf4, 0.82. Anal. Calcd. for C16H22N2O5 : C, 59.61; H, 6.88; N, 8.69%. Found C, 59.43; H, 6.88; N, 8.35%

후처리

  1. stirringstirred overnight at room temperature
  2. customAfter removing the solvent
  3. extractionextracted with acid and base
  4. customChloroform was removed under reduced pressure
  5. customtriturated with pet. ether
  6. filtrationfiltered
  7. washwashed with pet. ether
  8. customdried

출처 및 근거

ORD 기록
ord-f3d2146e602044d387d3409607c9d625
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05032271

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