Water → HCID 69516582, compound

HRID 971160Notes

Reaction equation

HRID 971160 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[C:17]([O:21][C:22](=[O:29])[NH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:26]3[CH2:27][CH2:28][CH:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:29])[CH2:25]3)=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 59020005HCID 59020005, compound

Product 1

HCID 69516582HCID 69516582, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Part A. 1-(4-Chlorocarbonyl-phenyl)-cyclopropanecarboxylic acid methyl ester (0.78 g, 3.28 mmol), pyrrolidin-3-yl-carbamic acid tert-butyl ester (0.60 g, 3.22 mmol) and DIEA (1.18 mL, 6.44 mmol) were stirred in CH2Cl2 (10 mL) at rt under N2 overnight. H2O was added. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, filtered, dried in vacuo. The residue was dissolved in MeOH (20 mL) and 1N NaOH (10 mL) was added. The reaction was heated at 50° C. for 2.5 h. The solvents were evaporated. The residue was extracted with Et2O, the H2O layer was acidified with citric acid, and extracted with Et2O (2×), washed with brine, dried over MgSO4, filtered, and concentrated to dryness to yield 1-[4-(3-tert-butoxycarbonylamino-pyrrolidine-1-carbonyl)-phenyl]-cyclopropanecarboxylic acid methyl ester (1.08 g, yield: 83.0%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customdried in vacuo
  6. dissolutionThe residue was dissolved in MeOH (20 mL)
  7. addition1N NaOH (10 mL) was added
  8. customThe solvents were evaporated
  9. extractionThe residue was extracted with Et2O
  10. extractionextracted with Et2O (2×)
  11. washwashed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-345ca9fb418e4360a11ccf0fefc2e685
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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