Dimethylformamide → 4-(Pyridin-4-yl)butanoyl-sarcosine 3(R)-[2-(indol-3-yl)ethyl]-beta-alanine ethyl ester

HRID 618150Notes

Reaction equation

HRID 618150 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([N:12]([CH2:14][C:15]([OH:17])=[O:16])[CH3:13])=[O:11])=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.[N:25]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.CN1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.CN(C=[O:56])C>CCOC(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][C:10]([N:12]([CH2:14][C:15]([OH:17])=[O:16])[CH3:13])=[O:11])=[CH:5][CH:6]=1.[CH2:50]([O:49][C:48](=[O:56])[CH2:47][C@@H:2]([CH2:3][CH2:4][C:5]1[C:28]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:25][CH:6]=1)[NH2:1])[CH3:51]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 206892654-(Pyridin-4-yl)butanoyl-sarcosine

Product 1

HCID 867544774-(Pyridin-4-yl)butanoyl-sarcosine 3(R)-[2-(indol-3-yl)ethyl]-beta-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acid 6-2 (288 mg, 1.22 mmol), amine 4-4 (318 mg, 1.22 mmol), BOP (647 mg, 1.5 mmol), and NMM (462 μL, 4.2 mmol) were combined in 6 mL DMF. After stirring overnight the mixture was diluted with EtOAc, washed with water (4×), sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, EtOAc then 5% MeOH/EtOAc) provided 6-3 as an orange oil.

Workup

  1. washwashed with water (4×), sat. NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28a9d7fc62524042a73a9e61bd71b527
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

Loading…