Hydrochloric Acid → 1-{[2-(Hex-5-enylmethylcarbamoyl)-4-hydroxycyclopentanecarbonyl]amino}-2-vinylcyclopropanecarboxylic acid

HRID 570119Notes

Reaction equation

HRID 570119 reaction equation
C([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([OH:19])[CH2:16][CH:15]2[C:20](=[O:29])[N:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28])[CH3:22])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-].Cl>CN(C=O)C>[CH2:23]([N:21]([CH3:22])[C:20]([CH:15]1[CH2:16][CH:17]([OH:19])[CH2:18][CH:14]1[C:12]([NH:11][C:6]1([C:4]([OH:5])=[O:3])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:13])=[O:29])[CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 668706071-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 668702741-{[2-(Hex-5-enylmethylcarbamoyl)-4-hydroxycyclopentanecarbonyl]amino}-2-vinylcyclopropanecarboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Compound 6 (493 mg, 1.21 mmol) was dissolved in DMF (1 mL) and transferred to a 20 mL microwave reaction vessel. Then, aqueous LiOH (2 M, 10.5 mL) and a stirbar were added. The reaction vessel was sealed and the immiscible slurry was shaken vigorously before insertion in the microwave cavity. The reaction was irradiated for 30 min to 130° C. The reaction mixture was cooled to 40° C. and the clear solution acidified to pH 2 with aqueous HCl (1 M, 24 mL) and extracted 3 times with EtOAc (20 mL). The pooled organic layers were washed with brine, dried (MgSO4) and filtered. The solvent was evaporated in vacuo to afford compound 7 (410 mg, 90%). LC/MS (Method A): tR=2.46 min, >95%, m/z (ESI+)=379 (MH+).

Workup

  1. customtransferred to a 20 mL microwave reaction vessel
  2. customThe reaction vessel was sealed
  3. customThe reaction was irradiated for 30 min to 130° C
  4. extractionextracted 3 times with EtOAc (20 mL)
  5. washThe pooled organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0384043e43ac4bad8eb339fcffc9b52d
Source dataset
uspto-grants-2015_05
Patent number
US09023808B2

Reaction notes

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