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

HRID 1602621Notes

Reaction equation

HRID 1602621 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.[CH3:31][C:32]#[N:33].F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49]C=2N=N1.[CH3:61][CH2:62][O:63][C:64](C)=[O:65]>>[CH2:62]([O:63][C:64](=[O:65])[CH2:31][C@@H:32]([C:48]1[CH:49]=[N:41][CH:45]=[CH:46][CH:47]=1)[NH:33][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 86754780(2-Oxo-3-(2-(5,6,7,8-tetrahydro[1,8]-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)acetyl-3(S)-pyridin-3-yl-beta-alanine ethyl ester

Procedure

To a stirred solution of 2-8 (50 mg, 0.15 mmol), 2-10 (44 mg, 0.17 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), 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 2-12 as a brown oil.

Workup

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

Sources & evidence

ORD record
ord-88b7b259eb2d42c79e2492979a653d7e
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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