Sodium Hydroxide → 3-Cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic Acid

HRID 858880Notes

Reaction equation

HRID 858880 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:27])[CH2:7][C:8]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)([OH:21])[CH2:9][CH2:10][NH:11][C:12](=[O:20])[CH2:13][CH2:14][C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)C>C(Cl)Cl>[CH:22]1([C:8]([OH:21])([CH2:9][CH2:10][NH:11][C:12](=[O:20])[CH2:13][CH2:14][C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[CH2:7][C:6]([OH:27])=[O:5])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 587623263-Cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic acid ethyl ester

Product 1

HCID 587627253-Cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic AcidYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of NaOH (0.3 M, 1.6 mL, 0.49 mmol) was added to 3-cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic acid ethyl ester (86 mg, 0.245 mmol) from Step 1 below and stirred at room temperature until complete by HPLC. The reaction was diluted with 10 mL CH2Cl2, and washed with 10 mL saturated NH4Cl. The aqueous layer was extracted with 2×10 mL CH2Cl2, and the organic layers were combined. After concentrating by rotary evaporation, the residue was purified by flash chromatography to give the desired compound (29 mg, 37% yield).

Workup

  1. washwashed with 10 mL saturated NH4Cl
  2. extractionThe aqueous layer was extracted with 2×10 mL CH2Cl2
  3. concentrationAfter concentrating by rotary evaporation
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-df6ace67726742fa87ad133e47f57c1c
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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