Acetonitrile → HCID 86754490, compound

HRID 618174Notes

Reaction equation

HRID 618174 reaction equation
[NH:1]1[C:10]2[C:5](=[C:6]([CH2:11][CH2:12][CH2:13][C:14]([N:16]([CH:21]3[CH2:23][CH2:22]3)[CH2:17][C:18]([OH:20])=O)=[O:15])[CH:7]=[CH:8][N:9]=2)[CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.CC#N.CN([P+](O[N:45]1N=N[C:47]2[CH:48]=CC=C[C:46]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:61]([O:64][CH2:65][CH3:66])(=[O:63])[CH3:62]>>[CH2:65]([O:64][C:61](=[O:63])[CH2:62][C@@H:46]([C:47]#[CH:48])[NH:45][C:18](=[O:20])[CH2:17][N:16]([C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH2:2][NH:1]2)[CH:21]1[CH2:23][CH2:22]1)[CH3:66]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 20689261HCID 20689261, compound

Product 1

HCID 86754490HCID 86754490, compound

Procedure

To a stirred solution of acid 23-6 (40 mg, 0.1256 mmol), amine 21-6 (33 mg, 0.1884 mmol), NMM (70 μl, 0.5024 mmol) and CH3CN (1 ml) was added BOP reagent (61 mg, 0.1382 mmol). After 20 h at ambient temperature, the solution was diluted with ethyl acetate and then washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 40:1:1 CH2Cl2 /MeOH/AcOH) gave the ester 23-7 as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-c9b3642a6827453a927900f0327a7c6d
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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