Sodium Carbonate → HCID 86620429, compound

HRID 1907763Notes

Reaction equation

HRID 1907763 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7](Cl)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[NH:18]1[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1.F[C:25]1[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=1>C(Cl)Cl>[CH2:10]([O:9][C:7]([NH:23][C@@H:20]1[CH2:21][CH2:22][N:18]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[CH:27][CH:26]=2)[CH2:19]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 1519352(3R)-pyrrolidin-3-amineHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 86620429HCID 86620429, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Na2CO3 (7.81 g, 73.7 mmol) then CbzCl (6.88 mL, 48.2 mmol) was added to a solution of 399 (10.28 g, 39.2 mmol) (399 was synthesized following the procedure J starting from (R)-pyrrolidin-3-amine and tert-butyl 4-fluorobenzoate) in DCM (196 mL) at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for 16 h. It was then quenched with saturated NH4Cl, stirred for 30 min, diluted with DCM, washed with brine then H2O, dried with MgSO4, filtered and concentrated to afford the title compound 400 (16.4 g, quant.) as a beige solid.

Workup

  1. customwas synthesized
  2. customat 0° C
  3. customIt was then quenched with saturated NH4Cl
  4. stirringstirred for 30 min
  5. additiondiluted with DCM
  6. washwashed with brine
  7. dry with materialH2O, dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-730d7d212b6d473bbe35cd0f400eea84
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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