Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 59737479, compound

HRID 1907756Notes

Reaction equation

HRID 1907756 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.Br[C:51]1[CH:56]=[CH:55][C:54]([NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[C:53]([N+:65]([O-])=O)[CH:52]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:65][C:53]3[CH:52]=[C:51]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:56]=[CH:55][C:54]=3[NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:19])=[CH:21][CH:22]=2)[CH2:10]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 52904808tert-Butyl (4-bromo-2-nitrophenyl)carbamateHCID 59737566HCID 59737566, compound

Product 1

HCID 59737479HCID 59737479, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The acid 325 (3.23 g, 7.03 mmol) and BOP (4.66 g, 10.55 mmol) were added to a solution of 322 (1.2 g, 7.03 mmol) (Compound 322 was synthesized following general procedures B and C starting from compound 2 and phenylboronic acid) in pyridine (40 mL). The reaction mixture was stirred at room temperature for 24 h, concentrated under reduced pressure, diluted with DCM, washed with water, NaHCO3 and brine. The residue was purified by flash chromatography (2-4% MeOH in DCM) to give the title compound 326 (1.74 g, 43%) as a brown solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with DCM
  3. washwashed with water, NaHCO3 and brine
  4. customThe residue was purified by flash chromatography (2-4% MeOH in DCM)

Sources & evidence

ORD record
ord-3a9c5f6429114c02a2178e4586f5e1c7
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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