Pyridine → HCID 69854077, compound

HRID 2084541Notes

Reaction equation

HRID 2084541 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].N1C=CC=CC=1>C(Cl)Cl>[CH2:34]([O:33][C:31](=[O:32])[NH:20][C:17]1[CH:16]=[CH:15][C:14]([C:13](=[O:21])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:22])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:19][CH:18]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 60077744HCID 60077744, compound

Product 1

HCID 69854077HCID 69854077, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1(S)-(4-aminobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester (67 mg, 0.22 mmol) and triethylamine (95 μL, 0.69 mmol) in DCM (3 mL) was cooled on an ice bath prior to addition of benzyl chloroformate (98 μL, 0.69 mmol). The reaction was warmed to room temperature and left for 15 hours. Examination by T.l.c. suggested minimal conversion to product hence pyridine (0.10 mL, 1.2 mmol) was added and the reaction left for a further 2 hours. Solvent was removed in vacuo and the residue taken up in ethyl acetate (20 mL). The organic phase was washed with 1M HCl (1×20 mL), brine (1×20 mL), 1M Na2CO3 (1×20 mL) and brine (1×20 mL, dried over MgSO4, filtered and the solvent removed in vacuo, giving a yellow solid. Purification by column chromatography (SiO2, 9:1 isohexane:ethyl acetate) afforded the title compound as a yellow solid (90 mg, 90%).

Workup

  1. additionwas added
  2. waitthe reaction left for a further 2 hours
  3. customSolvent was removed in vacuo
  4. washThe organic phase was washed with 1M HCl (1×20 mL), brine (1×20 mL), 1M Na2CO3 (1×20 mL) and brine (1×20 mL
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customgiving a yellow solid
  9. customPurification by column chromatography (SiO2, 9:1 isohexane:ethyl acetate)

Sources & evidence

ORD record
ord-af6dfb364b084f39ab47668574557048
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

Loading…