Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 178440682, compound

HRID 1424141Notes

Reaction equation

HRID 1424141 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]1[C:8](O)=O.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH2:22])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CC(N(C)C)=O>[C:11]([C:15]1[CH:20]=[CH:19][C:18]2[NH:21][C:8]([CH:3]3[CH:2]([OH:1])[CH2:7][CH2:6][CH2:5][NH:4]3)=[N:22][C:17]=2[CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4327084-Tert-butylbenzene-1,2-diamineHCID 138742223-Hydroxypipecolic acid

Product 1

HCID 178440682HCID 178440682, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A 0.2M solution of 3-hydroxypiperidine-2-carboxylic acid (500 μL, 100 μmol) in DMA was added to a 0.2M solution of 4-tert-butyl-1,2-diaminobenzene (500 μL, 100 μmol) in DMA followed by BOP (44 mg, 100 μmol). The reaction was stirred at room temperature for 16 hours before concentrating in vacuo. A solvent mixture of THF/AcOH (5/1, 1 mL) was added to the residue, and the reaction heated to 60° C. for 16 hours. The reaction was cooled, concentrated in vacuo, dissolved in DMSO (1 mL) and purified using preparative HPLC (XTERRA-C18 (250×19 mm, 10μ, mobile phase A: Acetonitrile, mobile phase B: 10 mM ammonium acetate in water; eluting with a gradient of 10-70% organic with a flow rate of 16 mL/min over 18 minutes) to afford the title compound.

Workup

  1. concentrationbefore concentrating in vacuo
  2. additionA solvent mixture of THF/AcOH (5/1, 1 mL)
  3. additionwas added to the residue
  4. temperaturethe reaction heated to 60° C. for 16 hours
  5. temperatureThe reaction was cooled
  6. concentrationconcentrated in vacuo
  7. dissolutiondissolved in DMSO (1 mL)
  8. custompurified
  9. washeluting with a gradient of 10-70% organic with a flow rate of 16 mL/min over 18 minutes)

Sources & evidence

ORD record
ord-4e928b8bdce742548ea748c32771d20b
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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