Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 57842848, compound

HRID 735713Notes

Reaction equation

HRID 735713 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:28][C:29]1[CH:30]=[C:31]([CH:78]=[CH:79][CH:80]=1)[CH2:32][NH:33][C:34](=[O:77])[CH:35]([C:62]1[CH:76]=[CH:75][C:65]([CH2:66][N:67]([CH2:71][C:72](O)=[O:73])[C:68](=[O:70])[CH3:69])=[CH:64][CH:63]=1)[NH:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[C:43]([N:47]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[N:42][CH:41]=[CH:40]2>C(Cl)Cl.CN(C=O)C>[C:68]([N:67]1[CH2:66][C:65]2=[CH:64][CH:63]=[C:62]([CH:76]=[CH:75]2)[CH:35]([NH:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[C:43]([N:47]([C:48]([O:50][C:51]([CH3:53])([CH3:54])[CH3:52])=[O:49])[C:55]([O:57][C:58]([CH3:60])([CH3:59])[CH3:61])=[O:56])=[N:42][CH:41]=[CH:40]3)[C:34](=[O:77])[NH:33][CH2:32][C:31]2[CH:30]=[C:29]([CH:80]=[CH:79][CH:78]=2)[NH:28][C:72](=[O:73])[CH2:71]1)(=[O:70])[CH3:69]

Participants

5

Reactant 2

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57842679HCID 57842679, compound

Product 1

HCID 57842848HCID 57842848, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of BOP (30 mg, 0.065), TEA (0.07 mL, 0.5 mmol) in 40 mL of CH2Cl2, was added a solution of 80F (40 mg, 0.055 mmol) in DMF (8 mL) via a syringe pump over 6 h. The mixture was stirred r.t over night, then was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-10% MeOH/CH2Cl2) afforded 80G (21 mg, 54%). MS (ESI) m/z 709.5 (M+H)+.

Workup

  1. customwas quenched with sat. NH4Cl
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification via flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5f87efbf4fef481e9c47f2004097e58c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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