Pyridine → HCID 67248809, compound

HRID 1035320Notes

Reaction equation

HRID 1035320 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][C:21](=[O:31])[CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:19].Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1>ClCCl>[CH2:24]([N:23]([CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:31])[C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 80908N-Benzylglycine ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14037596D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 4-methyl ester

Product 1

HCID 67248809HCID 67248809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 255B (31.28 g, 126.6 mmol) in dichloromethane (500 mL) was added N-benzylglycine ethyl ester (24.46 g, 126.6 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (24.3 g, 126.6 mmol), and pyridine (70 mL). After addition of the reagents, the reaction was allowed to warm to ambient temperature and stirred for 16 hours. The solution was concentrated and then partitioned between ethyl acetate and HCl (1 M, aqueous). The organic solvent was collected, and the aqueous again washed with ethyl acetate. The organic solvent was combined, washed with K2CO3 (2 M aqueous), washed with brine, and dried with MgSO4. Concentration of the dried solution afforded the title compound.

Workup

  1. additionAfter addition of the reagents
  2. concentrationThe solution was concentrated
  3. custompartitioned between ethyl acetate and HCl (1 M, aqueous)
  4. customThe organic solvent was collected
  5. washthe aqueous again washed with ethyl acetate
  6. washwashed with K2CO3 (2 M aqueous)
  7. washwashed with brine
  8. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-994122d4b9b843f28fd6fe5f87f6a6ac
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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