Potassium Carbonate → HCID 67093153, compound

HRID 1261852Notes

Reaction equation

HRID 1261852 reaction equation
C([O:5][C:6]([N:8]1[CH:12]([CH2:13][N:14]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C@H:15](C(OC)=O)[CH3:16])[CH2:11][CH2:10][C@H:9]1[CH2:31][CH:32]=[CH2:33])=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>Cl>[CH2:24]([O:23][C:21]([N:14]1[C@@H:15]([CH3:16])[C:6](=[O:5])[N:8]2[CH:9]([CH2:31][CH:32]=[CH2:33])[CH2:10][CH2:11][C@H:12]2[CH2:13]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67093023HCID 67093023, compound

Product 1

HCID 67093153HCID 67093153, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (S)-2-allyl-5-{[benzyloxycarbonyl-((S)-1-methoxycarbonyl-ethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (298 mg, 0.65 mmol) in hydrogen chloride solution (4 M in 1,4-dioxane, 3 mL) was stirred at room temperature for 2 h, then evaporated. The residue was taken up in MeOH (3 mL), then after addition of potassium carbonate (268 mg, 1.94 mmol) the suspension was stirred at room temperature for 16 h, then partitioned between sat. aq. ammonium chloride solution and EtOAc. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to afford the title compound (221 mg, 100%). Light brown solid, MS: 329.4 (M+H)+.

Workup

  1. customevaporated
  2. custompartitioned between sat. aq. ammonium chloride solution and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2c8d2cc315b144678e35b970e34b1ad7
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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