Hydrochloric Acid → (+/-)-1-BOC-amino-2-cyclopentene-4-carboxylic Acid

HRID 1274432Notes

Reaction equation

HRID 1274432 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4]1.[OH-].[Na+].[C:13]([O:17][C:18](F)=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl>O.O1CCOCC1.C(OCC)C>[C:18]([C:3]1([NH2:2])[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4]1)([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9898818Tert-butyloxycarbonyl fluoride2×HCID 101712614-Aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Product 1

HCID 77801814(+/-)-1-BOC-amino-2-cyclopentene-4-carboxylic AcidYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

16.4 g of crude (±)-1-amino-2-cyclopentene-4-carboxylic acid hydrochloride (prepared as in J. Org. Chem. 1981, 46, 3268) were dissolved in a mixture of 80 ml of water and 80 ml of dioxane at room temperature under nitrogen. The mixture was then adjusted to pH 14 with 1N NaOH, and a diethyl ether solution of tert-butyloxycarbonyl fluoride (BOC-F, 20% excess) was added (BOC-F prepared as in Synthesis 1975, 599). The mixture was stirred for a further 5 h at room temperature. The pH was adjusted to 2 with conc. HCl. After distillation of the organic solvents, 50 ml of water were added to the residue, and the mixture was extracted 3 times with 100 ml of ethyl acetate. The organic phase was evaporated to 50 ml and diluted with 25 ml of toluene. After cooling (0-10° C.), the title compound was filtered and dried. 14.3 g of product were obtained. The yield was 63%.

Workup

  1. distillationAfter distillation of the organic solvents, 50 ml of water
  2. additionwere added to the residue
  3. extractionthe mixture was extracted 3 times with 100 ml of ethyl acetate
  4. customThe organic phase was evaporated to 50 ml
  5. additiondiluted with 25 ml of toluene
  6. temperatureAfter cooling (0-10° C.)
  7. filtrationthe title compound was filtered
  8. customdried

Sources & evidence

ORD record
ord-b0b4dc3342974f928074f7ea4dd927dd
Source dataset
uspto-grants-2000_12
Patent number
US06156893

Reaction notes

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