Potassium Carbonate → HCID 86654423, compound

HRID 1844319Notes

Reaction equation

HRID 1844319 reaction equation
C([O:4][C:5]1([C@:9]2([C:29]([N:31]3[CH2:36][C@@H:35]4[CH2:37][C@H:32]3[CH2:33][N:34]4[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:30])[CH2:13][CH2:12][C@@H:11]([N:14]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[C@@H:15]3[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]3)[CH2:10]2)[CH2:8][CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:41]([O:40][C:38]([N:34]1[CH2:33][C@@H:32]2[CH2:37][C@H:35]1[CH2:36][N:31]2[C:29]([C@@:9]1([C:5]2([OH:4])[CH2:6][CH2:7][CH2:8]2)[CH2:13][CH2:12][C@@H:11]([N:14]([C:23](=[O:28])[C:24]([F:26])([F:27])[F:25])[C@@H:15]2[C@H:20]([O:21][CH3:22])[CH2:19][O:18][CH2:17][CH2:16]2)[CH2:10]1)=[O:30])=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86654424HCID 86654424, compound

Product 1

HCID 86654423HCID 86654423, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.43 g (2.26 mmol) of 3-{[(1R,3S)-3-[1-(acetyloxy)cyclobutyl]-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}cyclopentyl](trifluoroacetyl)amino}-1,5-anhydro-2,3-dideoxy-4-O-methyl-D-erythro-pentitol and 1.60 g (11.6 mmol) of powdered potassium carbonate in 8 mL of methanol was stirred at ambient temperature for 18 h, then partitioned between dichloromethane and brine, with sufficient water to dissolve solids. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using acetate to provide 1.33 g (100%) of the title compound as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34-1.62 (m, 10H) 1.66-2.93 (m, 15H) 3.20-3.63 (m, 8H) 3.66-4.03 (m, 3H) 4.06-4.24 (m, 3H) 4.25-4.65 (m, 2H) 4.68-5.29 (m, 1H). TLC Rf 0.33 (EtOAc). LC-MS ES+ 590.3

Workup

  1. custompartitioned between dichloromethane and brine, with sufficient water
  2. dissolutionto dissolve solids
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80ad89784055418abb72be183817b934
Source dataset
uspto-grants-2015_02
Patent number
US08946413B2

Reaction notes

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