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

HRID 2384846Notes

Reaction equation

HRID 2384846 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-a47809f47f594252908baefb03d8ed93
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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