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

HRID 1453337Notes

Reaction equation

HRID 1453337 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). 1H NMR (CDCl3) δ: 1.39-1.75 (m, 8H), 2.00-2.09 (m, 2H), 2.39-2.52 (m, 5H), 2.90 (t, J=7.45 Hz, 2H), 3.29-3.40 (m, 2H), 5.96 (s, 1H), 6.2 (s, 1H), 6.31 (br, 1H), 7.23 (s, 1H). MS (ESI): 322 (M−H).

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-bf24be77b9284e01ac29fd902c34093b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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