Reaktion #1777164

ord-03f22af8cfc94d79bfa109898d5f90a8

Reaktionsgleichung

C/C1=C2/[N-][C@H]([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])OC2C(O)[C@@H](n3cnc4cc(C)c(C)cc43)O[C@H]2CO)[C@]2(C)N=C(/C(C)=C3N=C(/C=C4N=C1[C@@H](CCC(N)=O)C\4(C)C)[C@@H](CCC(N)=O)[C@]\3(C)CC(N)=O)[C@@H](CCC(N)=O)[C@]2(C)CC(N)=O.O.[Co+2]
B12a
CC(C)(C)OC(=O)NCC(=O)O
Boc-gly
On1nnc2ccccc21
HOBt
ClCCCl
EDC
→
C/C1=C2/[N-][C@H]([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])O[C@H]2[C@@H](O)[C@@H](n3cnc4cc(C)c(C)cc43)O[C@@H]2CO)[C@]2(C)N=C(/C(C)=C3N=C(/C=C4N=C1[C@@H](CCC(N)=O)C\4(C)C)[C@@H](CCC(N)=O)[C@]\3(C)CC(N)=O)[C@@H](CCC(N)=O)[C@]2(C)CC(N)=O.[Co].[OH3+]
B12b

Edukte

C/C1=C2/[N-][C@H]([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])OC2C(O)[C@@H](n3cnc4cc(C)c(C)cc43)O[C@H]2CO)[C@]2(C)N=C(/C(C)=C3N=C(/C=C4N=C1[C@@H](CCC(N)=O)C\4(C)C)[C@@H](CCC(N)=O)[C@]\3(C)CC(N)=O)[C@@H](CCC(N)=O)[C@]2(C)CC(N)=O.O.[Co+2]
B12a
CC(C)(C)OC(=O)NCC(=O)O
Boc-gly
On1nnc2ccccc21
HOBt
ClCCCl
EDC

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
CN1CCCC1=O
N-methylpyrrolidinone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with water and saturated aqueous sodium hydrogencarbonate twice
  2. 2
    TrocknenThe organics are dried over MgSO4
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated
  5. 5
    workup.ADDITIONThe residue is treated with excess 4 M HCl in dioxane and aged for 1 hour
  6. 6
    Sonstigethe solid is collected

Vorschrift

A solution of B12a (1 g, 3.7 mmol), Boc-gly (966 mg, 5.5 mmol) and HOBt (596 mg, 4.4 mmol) in N-methylpyrrolidinone (5 mL) is treated with EDC (845 mg, 845 mg, 4.4 mmol) and stirred for 1 hour. The reaction is then diluted with ethyl acetate and extracted with water and saturated aqueous sodium hydrogencarbonate twice. The organics are dried over MgSO4, filtered and evaporated. The residue is treated with excess 4 M HCl in dioxane and aged for 1 hour. The mixture is slurried with ether and the solid is collected to afford B12b; ESIMS m/z for (M+H)+ C12H18BrN4O2 calcd.: 329.1. found: 329.1.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08153635B2uspto-grants-2012_04