Diisopropylethylamine → 2-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1949594Notes

Reaction equation

HRID 1949594 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH:9]1[C:24](O)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:28][O:29][NH2:30].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:10][CH:9]1[C:24](=[O:25])[NH:30][O:29][CH3:28])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27567784-((Benzyloxy)carbonyl)-1-((tert-butoxy)carbonyl)piperazine-2-carboxylic acid

Product 1

HCID 873210322-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester (0.364 g, 1 mmol) in dichloromethane (3 mL) was added O-Methyl Hydroxylamine HCl (95 mg, 1.13 mmol), EDC HCl (0.3 g, 1.57 mmol) and DIEA (0.28 g, 2.17 mmol). The resulting mixture was stirred at room temperature overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/n-Hexane (30/70) to afford the title product.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with EtOAc/n-Hexane (30/70)

Sources & evidence

ORD record
ord-18481ddfe2264f99a312e875e5393805
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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