1,2-Dichloroethane → Cbz-Asp(O-tBu) Indanylglycine Val-OAllyl

HRID 1631428

Reaktionsgleichung

Reaktionsgleichung von HRID 1631428
[CH:1]1([NH:10][CH2:11][C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:15][C@H:16]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH:17]([CH3:19])[CH3:18].[NH:26]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[C@H:27]([C:36]([OH:38])=[O:37])[CH2:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].CN1CCOCC1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:26]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[C@H:27]([C:36]([OH:38])=[O:37])[CH2:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].[CH:1]1([NH:10][CH2:11][C:12]([OH:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:15][C@H:16]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH:17]([CH3:19])[CH3:18]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 131731717Indanylglycine Val-OAllyl

Produkt 1

HCID 131731718Cbz-Asp(O-tBu) Indanylglycine Val-OAllylAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Indanylglycine-Val-OAllyl (0.46 g, 1.3 mmol) and Z-L-Asp(OtBu)-OH (0.425 g, 1.3 mmol) were solvated in CH2Cl2 (4.5 mL) followed by addition of 4-methylmorpholine (1.45 mL, 1.01 eq), DMAP (14 mg, 0.09 eq) then EDC (0.251 g, 1.01 eq). The mixture was stirred for 1 hour 40 min. Then it was extracted using CH2Cl2/brine. The organic layer was dried over MgSO4, concentrates and purified by silica using a gradient of EtOAc/Hexane (10 to 80%) to get 0.578 g of the desired compound.

Aufarbeitung

  1. extractionThen it was extracted
  2. dry with materialThe organic layer was dried over MgSO4, concentrates
  3. custompurified by silica using a gradient of EtOAc/Hexane (10 to 80%)

Quellen und Nachweise

ORD-Eintrag
ord-4b2a8d836e8d469781ca961e9fadd121
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791235B2

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