Potassium Carbonate → HCID 131729651, compound

HRID 1695303Notes

Reaction equation

HRID 1695303 reaction equation
[CH3:1]/[CH:2]=[C:3]1/[CH2:4][CH:5]2[N:16]([CH2:17]/1)[C:14](=[O:15])[C:13]1[C:8](=[CH:9][C:10]([OH:20])=[C:11]([O:18][CH3:19])[CH:12]=1)[N:7]=[CH:6]2.[C:21](=[O:24])([O-])[O-].[K+].[K+].[C:27]([O:31][C:32]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[C:43]([CH2:45][O:46]S(C2C=CC(C)=CC=2)(=O)=O)[N:42]=[C:41]([CH2:57]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:40]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.[I-].[K+]>[C:27]([O:31][C:32]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:40]=[C:41]([CH2:57][O:20][C:10]2[C:11]([O:18][CH3:19])=[CH:12][C:13]3[C:14](=[O:15])[N:16]4[CH2:17][C:3](=[CH:2][CH3:1])[CH2:4][C@H:5]4[CH:6]=[N:7][C:8]=3[CH:9]=2)[N:42]=[C:43]([CH2:45][O:46][C:10]2[C:11]([O:24][CH3:21])=[CH:12][C:13]3[C:14](=[O:15])[N:16]4[CH2:17][C:3](=[CH:2][CH3:1])[CH2:4][C@H:5]4[CH:6]=[N:7][C:8]=3[CH:9]=2)[CH:44]=1)=[O:33])([CH3:28])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5856240PRETOMAYMYCINHCID 71496931HCID 71496931, compound

Product 1

HCID 131729651HCID 131729651, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
30 °C

Procedure

To a stirred solution of pre-tomaymycin (30 mg) in dimethylformamide (0.5 mL), were added potassium carbonate (45.7 mg), a solution of 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(tosyloxymethyl)-pyridine (41 mg) in dimethylformamide (0.5 mL) and potassium iodide (18.3 mg). The reaction was stirred for 20 h at 30° C. Solids were filtered off and washed with dimethylformamide (0.2 mL). Water (0.5 mL) was added to the combined dimethylformamide solution and formic acid was added until complete dissolution of the precipitate. The resulting solution was injected for HPLC purification according to method B1. The appropriate fractions were combined and concentrated by centrifugal evaporation over a Jouan Model RC10.10. apparatus to afford 8,8′-[4-(3-tert-butoxycarbonylaminopropyloxy)-2,6-pyridine-diylbis(methylenoxy)]-bis[(S)-2-eth-(E)-ylidene-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one] (8.3 mg).

Workup

  1. filtrationSolids were filtered off
  2. washwashed with dimethylformamide (0.2 mL)
  3. additionWater (0.5 mL) was added to the combined dimethylformamide solution and formic acid
  4. additionwas added until complete dissolution of the precipitate
  5. customThe resulting solution was injected for HPLC purification
  6. concentrationconcentrated by centrifugal evaporation over a Jouan Model RC10.10

Sources & evidence

ORD record
ord-7b69c926b35c453682abf1e131e0ad0c
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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