Propylphosphonic anhydride → HCID 178451399, compound

HRID 1480452Notes

Reaction equation

HRID 1480452 reaction equation
[NH2:1][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[NH:17]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])[N:19]=[N:18]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[NH:17]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][C:25]([NH:1][CH:2]2[CH2:3][CH:4]3[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]([CH2:6][CH2:5]3)[CH2:8]2)=[O:26])[N:19]=[N:18]1

Participants

5

Reactant 3

HCID 111923Propylphosphonic anhydrideHCID 22570519tert-Butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylateHCID 178525383HCID 178525383, compound

Product 1

HCID 178451399HCID 178451399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A reaction mixture comprising of tert-butyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (250 mg, 1.105 mmol), 4-(1H-1,2,3-triazol-4-yl)butanoic acid (Example 17, step 4) (171 mg, 1.105 mmol), T3P® 50% DMF (1.29 ml, 2.209 mmol) and TEA (462 μl, 3.31 mmol) in DMF (3.6 ml) was stirred for 4 hours. The reaction mixture was concentrated under reduced pressure. The resulting oil was diluted with DCM and washed with water. The organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. The material was taken crude to the next step.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting oil was diluted with DCM
  3. washwashed with water
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd7ec53ac1fc4a42b4887c2b8da51527
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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