Dimethylformamide → HCID 11668908, compound

HRID 2244977Notes

Reaction equation

HRID 2244977 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1NCC(O)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1.Cl.C([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1CN)(OC(C)(C)C)=O.F[P-](F)(F)(F)(F)F.[N:46]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:50]2C=CC=CC=2N=N1.[CH3:66][N:67]([CH:69]=[O:70])C>O.CCOC(C)=O>[NH:31]1[CH2:32][CH2:33][CH:34]([CH2:66][NH:67][C:69](=[O:70])[CH:50]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[NH:46][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[O:22])[CH2:35][CH2:36]1

Participants

8

Reactant 5

HCID 6228Dimethylformamide2×HCID 76934-Chlorophenyl IsocyanateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5171030N-o-FluorophenylglycineHCID 45072188tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 11668908HCID 11668908, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluorophenylglycine (59 mg, 0.35 mmol) in DMF (4 mL), 4-chlorophenylisocyanate (54 mg, 0.35 mmol) was added. The mixture was stirred at room temperature overnight. To the solution, a solution of N-BOC-aminomethylpiperidine hydrochloride (105 mg, 0.42 mmol) and TEA (0.150 mL, 1.08 mmol) in DMF (4 mL) was added, followed by addition of BOP (239 mg, 0.54 mmol). The mixture was then stirred at room temperature overnight. EtOAc and H2O were added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo.

Workup

  1. stirringThe mixture was then stirred at room temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fef33255059a4f9590e7a6568b4ed735
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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