Acetonitrile → (2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-ethynyl-beta-alanine ethyl ester

HRID 322503Notes

Reaction equation

HRID 322503 reaction equation
Cl.[O:2]=[C:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=3[N:11]=2)[CH2:6][CH2:5][N:4]1[CH2:20][C:21]([OH:23])=O.CN1CCOCC1.CC#N.F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2C=CC=[CH:49][C:44]=2N=N1.[CH3:61][CH2:62][O:63][C:64]([CH3:66])=[O:65]>>[CH2:62]([O:63][C:64](=[O:65])[CH2:66][C@@H:45]([C:44]#[CH:49])[NH:41][C:21](=[O:23])[CH2:20][N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[CH2:16][CH2:15][CH2:14][NH:13][C:12]=3[N:11]=2)[C:3]1=[O:2])[CH3:61]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 70226426(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetic acid hydrochloride

Product 1

HCID 86754778(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-ethynyl-beta-alanine ethyl ester

Procedure

To a stirred solution of 2-8 (50 mg, 0.15 mmol), 2-9 (29 mg, 0.17 mmol) (Zablocki et al., J. Med Chem., 1995, 38, 2378), NMM (83 μL, 0.75 mmol), and CH3CN (1 mL) was added BOP (74 mg, 0.17 mmol). After 20 h, the reaction mixture was diluted with EtOAc and then washed with sat. NaHCO3, H2O and brine, dried (MgSO4), and concentrated to give 2-11 as a yellow oil.

Workup

  1. washwashed with sat. NaHCO3, H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2a56651681d5492b8c240ce77634eb4d
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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