Sodium Carbonate → HCID 66743992, compound

HRID 1429593Notes

Reaction equation

HRID 1429593 reaction equation
[CH3:1][O:2][C:3](=[O:26])[NH:4][C:5]1[CH:21]=[C:20]2[C:8]([C:9]3[N:24]=[C:12]([C@@H:13]([NH2:23])[CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:22])[NH:19]2)[NH:11][C:10]=3[F:25])=[CH:7][CH:6]=1.[C:27](=[O:30])([O-])[O-:28].[Na+].[Na+]>CN(C=O)C.CO>[CH3:1][O:2][C:3](=[O:26])[NH:4][C:5]1[CH:21]=[C:20]2[C:8]([C:9]3[N:24]=[C:12]([C@@H:13]([NH:23][C:27]([O:28][C:8]([CH3:20])([CH3:9])[CH3:7])=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:22])[NH:19]2)[NH:11][C:10]=3[F:25])=[CH:7][CH:6]=1.[CH3:1][O:2][C:3](=[O:26])[NH:4][C:5]1[CH:21]=[C:20]2[C:8]([C:9]3[N:24]=[C:12]([C@@H:13]([NH2:23])[CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:22])[NH:19]2)[NH:11][C:10]=3[F:25])=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 66743992HCID 66743992, compound

Product 2

HCID 66743992HCID 66743992, compoundHCID 86662310HCID 86662310, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

I-20B. ((S)-14-Amino-17-fluoro-9-oxo-8,16,18-triaza-tricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl)-carbamic acid methyl ester: To a solution of I-20A (40 mg, 0.090 mmol) in DMF (3 mL) was added sodium carbonate (12.43 mg, 0.117 mmol) and 1-Fluoro-4-hydroxy-1,4 diazoniabicyclo[2,2,2]octanebis(tetrafluoroborate) (50% in alumina) (62.9 mg, 0.090 mmol) in a portion, respectively and the resulting solution was stirred for 2 h at rt. The reaction mixture was diluted with MeOH and purified by reverse phase chromatography which gave both ((S)-14-tert-Butoxycarbonylamino-17-fluoro-9-oxo-8,16,18-triaza-tricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl)-carbamic acid methyl ester and ((S)-14-Amino-17-fluoro-9-oxo-8,16,18-triaza-tricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl)-carbamic acid methyl ester. The mixture was dissolved in 4N HCl dioxane (10 mL) and stirred overnight at 50° C. Concentration of the solution provided 11 mg of I-20B (34%).

Workup

  1. custompurified by reverse phase chromatography which

Sources & evidence

ORD record
ord-3629ad8158fa48eaaca0f264f4c5c9ce
Source dataset
uspto-grants-2015_01
Patent number
US08940720B2

Reaction notes

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