Triethylamine → HCID 57488852, compound

HRID 2114365Notes

Reaction equation

HRID 2114365 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.CCN(CC)CC.[C:40]([NH:47][C@:48]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:50](O)=[O:51])[CH3:49])([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>CN(C=O)C>[C:56]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:55]=[CH:54][C:53]([C:48]([NH:47][C:40](=[O:41])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:49])[C:50](=[O:51])[N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:58][CH:57]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57183565(R)-2-((tert-butoxycarbonyl)amino)-2-phenylpropanoicacid

Product 1

HCID 57488852HCID 57488852, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BOP (880 mg, 2.0 mmol) was added to a mixture containing pyrrolidine (142 mg, 2.0 mmol), Et3N (279 ul, 2.0 mmol) and N-Boc-2-phenylalanine (570 mg, 1.67 mmol) in DMF (10 ml) and the resulting mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the residue was taken up in EtOAc and washed with brine, dried and concentrated. The crude product was purified by column chromatography (48 g silica gel 60,230-400 mesh, 20% EtOAc in hexane as eluent) to give 581 mg (75%) of the title compound as a white solid. MS(ES) m/e 395.6 [M+H]1

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (48 g silica gel 60,230-400 mesh, 20% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-5afe29fdc5f043879b6998fdb244651c
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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