Benzoyl chloride → HCID 58674951, compound

HRID 1809480Notes

Reaction equation

HRID 1809480 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@@H:7]([N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[C:16]1=[O:22])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:23])[C@@H:7]([N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]1=[O:22])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58674957HCID 58674957, compound

Product 1

HCID 58674951HCID 58674951, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of (S)-2-(3-amino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionic acid tert-butyl ester (2.6 g, 8.26 mmol) in dichloromethane (50 mL) was added triethylamine (918 mg, 9.09 mmol) and DMAP (20 mg) followed by dropwise addition of benzoyl chloride (1.27 g, 9.1 mmol). The reaction mixture was stirred at room temperature for 12 hours and then partitioned between EtOAc and sat. aqueous NH4Cl. The organic layer was washed with water (30 ml), brine (30 mL), dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (10-25% ethyl acetate/petrol ether) to afford the title compound as a colourless oil (2.07 g, 60%); 1H NMR (400 MHz, CDCl3) δ 1.48 (9H, s), 3.35 (1H, dd), 3.55 (1H, dd), 5.5 (1H, m), 6.26 (1H, t), 6.90 (1H, d), 7.15 (2H, m), 7.28 (3H, m), 7.52 (3H, m), 7.95 (2H, m), 8.52 (1H, d), 9.22 (1H, br s).

Workup

  1. custompartitioned between EtOAc and sat. aqueous NH4Cl
  2. washThe organic layer was washed with water (30 ml), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (10-25% ethyl acetate/petrol ether)

Sources & evidence

ORD record
ord-c8e6270f033c499d9e1066826276a85f
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

Loading…