Diisopropylethylamine → (1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl ester

HRID 2242428Notes

Reaction equation

HRID 2242428 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[C:7](=[O:12])[O:8]2)=[O:4].[NH2:13][C@H:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:16][CH3:17].CCN(C(C)C)C(C)C.OC1C=CC=CN=1>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][C@@H:9]([OH:8])[CH2:11][C@H:6]1[C:7](=[O:12])[NH:13][C@H:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:15][CH2:16][CH3:17])=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 12085932L-norvaline t-butyl esterHCID 592041763-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid methyl esterHCID 178516071HCID 178516071, compound

Product 1

HCID 59204201(1R,2R,4S)-2-((S)-1-tert-Butoxycarbonyl-butylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 41 (263 mg, 1.55 mmol) and H-Nva-OtBu (420 mg, 2.42 mmol) were dissolved in dry THF (20 mL). DIEA (530 uL, 3.04 mmol) and 2-hydroxypyridine (260 mg, 2.73 mmol) were added and the mixture was refluxed for five days. The solvent was evaporated and the crude product was purified by flash column chromatography (toluene/EtOAc 1:2) to give 42 (510 mg, 96%).

Workup

  1. temperaturethe mixture was refluxed for five days
  2. customThe solvent was evaporated
  3. customthe crude product was purified by flash column chromatography (toluene/EtOAc 1:2)

Sources & evidence

ORD record
ord-5b184a53ff8942a4a032557eedd603f0
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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