Water → HCID 44608949, compound

HRID 1961363Notes

Reaction equation

HRID 1961363 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[NH2:15][C:16]1[C:21]2=[C:22]([C:35]#[N:36])[CH:23]=[C:24]([C@@H:25]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@@:26]3([CH3:34])[OH:27])[N:20]2[N:19]=[CH:18][N:17]=1.O>CCO>[NH2:15][C:16]1[C:21]2=[C:22]([C:35](=[S:2])[NH2:36])[CH:23]=[C:24]([C@@H:25]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@@:26]3([CH3:34])[OH:27])[N:20]2[N:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 25001248HCID 25001248, compound

Product 1

HCID 44608949HCID 44608949, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

to anhydrous EtOH (30 μl) was added P2S5 (7.30 mg, 0.02 mmol) and the mixture stirred in a sealed vial for 1 h at RT. To the reaction mixture was added a solution of Compound 14 (51 mg, 0.0033 mmol) in anhydrous EtOH. (30 μl). The mixture was heated in a sealed vial at 120° C. for 3 h and then cooled to RT, whereupon water was added and the mixture extracted with DCM. The aqueous layer was concentrated to dryness and the residue purified by column chromatography silica gel (elution gradient ethyl acetate to 17% methanol in ethyl acetate) to afford Compound 21: ESI-MS m/z 340 ([M+H]+).

Workup

  1. temperatureThe mixture was heated in a sealed vial at 120° C. for 3 h
  2. additionwas added
  3. extractionthe mixture extracted with DCM
  4. concentrationThe aqueous layer was concentrated to dryness
  5. customthe residue purified by column chromatography silica gel (elution gradient ethyl acetate to 17% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-fb79d82202324c03a7c88972c82fc8f2
Source dataset
uspto-grants-2013_04
Patent number
US08415309B2

Reaction notes

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