Reaktion #61309

ord-4d9ce3e70f4a4423a9179679d6017a3d

Reaktionsgleichung

CCOC(=O)C1=C(c2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]1N2C(=O)OC(C)(C)C(Cl)(Cl)Cl
H7
CCOC(=O)C1=C(c2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]1N2C(=O)OC(C)(C)C(Cl)(Cl)Cl
(rac.)-(1R*,5S*)-7-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester
CCN(C(C)C)C(C)C
DIPEA
CC(=O)Cl
acetyl chloride
C1COCCO1.Cl
HCl dioxane
→
CCOC(=O)C1=C(c2ccc(OCCO)cc2)C[C@@H]2CN(C(C)=O)C[C@H]1N2C(=O)OC(C)(C)C(Cl)(Cl)Cl
(rac.)-(1R*,5S*)-3-Acetyl-7-[4-(2-hydroxyethoxy)phenyl]-3,9-diazabicyclo-[3.3.1]non-6-ene-6,9-dicarboxylic acid 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

Edukte

CCOC(=O)C1=C(c2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]1N2C(=O)OC(C)(C)C(Cl)(Cl)Cl
H7
CCOC(=O)C1=C(c2ccc(OCCO[Si](C)(C)C(C)(C)C)cc2)C[C@@H]2CN(C(=O)OC(C)(C)C)C[C@H]1N2C(=O)OC(C)(C)C(Cl)(Cl)Cl
(rac.)-(1R*,5S*)-7-{4-[2-(tert-Butyldimethylsilanyloxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester
CCN(C(C)C)C(C)C
DIPEA
CC(=O)Cl
acetyl chloride
C1COCCO1.Cl
HCl dioxane

Reagenzien

CN(C)c1ccncc1
DMAP

Lösungsmittel

CO
MeOH
C1CCOC1
THF
ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification of the residue by FC (EtOAc/heptane 1:1→EtOAc MeOH/EtOAc 1:9)

Vorschrift

As for compound S1, from H7 (5.80 g, 7.73 mmol), CH2Cl2 (60 mL), 4M HCl/dioxane (60 mL), THF (50 mL), DMAP (47 mg, 0.384 mmol), DIPEA (5.29 mL, 31.7 mmol), acetyl chloride (0.604 mL, 8.08 mmol), and MeOH (5 mL). Purification of the residue by FC (EtOAc/heptane 1:1→EtOAc MeOH/EtOAc 1:9) led to the title compound (3.07 g, 69%). Rf=0.20 (EtOAc). LC-MS: Rt=4.80; ES+: 576.93.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07427613B2uspto-grants-2008_09