Ethoxalyl chloride → HCID 86691687, compound

HRID 1407049Notes

Reaction equation

HRID 1407049 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].Cl[C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[C:20]([O:19][C:18]([NH:17][CH:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[CH2:11][NH:10][C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])([CH3:21])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 81531DiisopropylethylamineHCID 53486461tert-Butyl [2-(aminomethyl)cyclopentyl]carbamate

Product 1

HCID 86691687HCID 86691687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

iPr2NEt (0.5 mL) was added into a solution of tert-butyl (2-(aminomethyl)cyclopentyl)carbamate (300 mg) and ethyl 2-chloro-2-oxoacetate (191 mg) in THF (10 mL). The reaction was stirred at room temperature for 16 hours before being quenched by water. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic phase was dried over MgSO4 and concentrated under vacuum to give the crude ethyl 2-(((2-((tert-butoxycarbonyl)amino)cyclopentyl)methyl)amino)-2-oxoacetate which was used as was.

Workup

  1. custombefore being quenched by water
  2. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d67f042d66de46a68be52e5ec640668b
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

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