HCID 3431203, compound → HCID 59424582, compound

HRID 1261217Notes

Reaction equation

HRID 1261217 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][NH:6][CH2:7][CH2:8][O:9][CH3:10].[C:14]([O:18][C:19](=O)[O:20]C(C)(C)C)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][N:6]([CH2:7][CH2:8][O:9][CH3:10])[C:19](=[O:20])[O:18][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 3431203HCID 3431203, compoundHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 59424582HCID 59424582, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 64 (997 mg, 4 mmol) in CH2Cl2 (12 mL), di-tert-butylcarbonate (1.8 g, 8 mmol) was added and the reaction mixture was stirred for 3 hrs (scheme 14). DMAP (cat.) was added to the solution and the reaction mixture was allowed to stir for additional 76 hours. Solvent was removed under reduced pressure and the crude product was purified by column chromatography, eluent EtOAc/hexane (1:10) to afford the title compound 65 (778 mg, 56% yield) as a colorless oil. MS (m/z): 368.1/370.1 (M+Na).

Workup

  1. stirringto stir for additional 76 hours
  2. customSolvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography, eluent EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-28365bc3a52b480ba852c55c6a2a8f89
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

Loading…