Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 89500248, compound

HRID 2178501Notes

Reaction equation

HRID 2178501 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15](O)=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N.N.C[N:25]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[C:15]([C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=1[CH:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)(=[O:16])[NH2:25]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6857397HCID 6857397, compoundHCID 53435658HCID 53435658, compound

Product 1

HCID 89500248HCID 89500248, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]benzoic acid a1-3 (5.5 g, 19 mmol, 1 eq) in dichloromethane (150 ml) is saturated, at 0° C., with gaseous ammonia NH3 for 1 hour. BOP reagent (8.82 g, 19.9 mmol, 1.05 eq) is added portionwise to this solution. The reaction mixture is warmed to room temperature and stirred overnight. The reaction mixture is filtered off and the solid washed with dichloromethane (100 ml). The organic layer is evaporated under vacuum and the residue obtained is purified by chromatography over silicagel (eluent: CH2Cl2/MeOH 98.5/1.5) to give 5.4 g of tert-butyl 3-(2-carbamoylphenyl)pyrrolidine-1-carboxylate a1-4.

Workup

  1. filtrationThe reaction mixture is filtered off
  2. washthe solid washed with dichloromethane (100 ml)
  3. customThe organic layer is evaporated under vacuum
  4. customthe residue obtained
  5. customis purified by chromatography over silicagel (eluent: CH2Cl2/MeOH 98.5/1.5)

Sources & evidence

ORD record
ord-50384a1b5a5a46c4b3b3df4c2cf2bb6e
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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