1,2-Dichloroethane → Methyl 1-[(2-(s)-hydroxy-3-methylbutanoylamino)methyl]cyclopentanecarboxylate

HRID 51069Notes

Reaction equation

HRID 51069 reaction equation
[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3](O)=[O:4].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:23][CH2:24][C:25]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O>[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH:23][CH2:24][C:25]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853180(S)-2-Hydroxy-3-methylbutanoic acidHCID 13285792Methyl 1-(aminomethyl)cyclopentanecarboxylate

Product 1

HCID 21303063Methyl 1-[(2-(s)-hydroxy-3-methylbutanoylamino)methyl]cyclopentanecarboxylateYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of (S)-2-hydroxy-3-methyl-butyric acid (300 mg, 2.5 mmol) in CH2Cl2/DMF (5:1, 20 mL) at 0° C. was added HOBT (382 mg, 2.5 mmol) and EDC (477 mg, 2.5 mmol). The mixture was stirred for 10 min then methyl 1-(aminomethyl)cyclopentanecarboxylate (321 mg, 2.25 mmol) and iPr2NEt (0.5 mL, 2.5 mmol) were added and stirring was continued for 3 h. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, 1N HCl, sat'd NaHCO3, dried over magnesium sulfate, concentrated, and purified using flash chromatography to give a white solid (420 mg, 72%). MS [M+H]+258.

Workup

  1. stirringstirring
  2. waitwas continued for 3 h
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water, 1N HCl
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-3800ba581a5841069c09c3bf0abe7ef9
Source dataset
uspto-grants-2004_03
Patent number
US06713476B2

Reaction notes

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