Trimethylsilyldiazomethane → HCID 14775497, compound

HRID 433871Notes

Reaction equation

HRID 433871 reaction equation
[CH3:1][CH2:2][NH:3][C:4]([C@H:6]1[O:10][CH:9]([N:11]2[C:15]3[N:16]=[C:17]([NH:21][CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:26][CH:25]=4)[N:18]=[C:19]([NH2:20])[C:14]=3[N:13]=[CH:12]2)[C@@H:8]([OH:35])[C@H:7]1[OH:36])=[O:5].[Si](C=[N+]=[N-])(C)(C)[CH3:38].CO.O>CO.C(Cl)Cl>[CH3:38][O:33][C:32](=[O:34])[CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][NH:21][C:17]2[N:16]=[C:15]3[C:14]([N:13]=[CH:12][N:11]3[CH:9]3[CH:8]([OH:35])[CH:7]([OH:36])[CH:6]([C:4](=[O:5])[NH:3][CH2:2][CH3:1])[O:10]3)=[C:19]([NH2:20])[N:18]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 22242641Methanol--water (1/1)HCID 44366731HCID 44366731, compound

Product 1

HCID 14775497HCID 14775497, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The methyl ester, JR2171, was synthesized by dissolving approximately 10.0 mg of 3-(4-{2-[6-amino-9-(5-ethylcarbamoyl-3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-ylamino]-ethyl}-phenyl)-propionic acid (CGS21680) in 5 mL 10% MeOH/CH2Cl2 and adding TMS Diazomethane (2.0 M solution in hexanes) dropwise until a yellow color persisted. After stirring for 30 minutes the solvent was removed under reduced pressure. The crude compound was then purified by HPLC using a C18 column and a MeOH/H2O gradient, yielding 6.7 mg of compound (66% yield). Characterization by HRMS, APCI MS, 1H NMR, and 13C NMR were consistent with the putative structure.

Workup

  1. customwas removed under reduced pressure
  2. customThe crude compound was then purified by HPLC

Sources & evidence

ORD record
ord-6b66a5be38b941749b011f11075abf97
Source dataset
uspto-grants-2003_12
Patent number
US06670334B2

Reaction notes

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