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

HRID 390123Notes

Reaction equation

HRID 390123 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 1c (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 the title compound (410 mg, 90%). LC/MS >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-5da196206360430eaaa9852d18008c11
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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