4-Methylmorpholine → HCID 131720343, compound

HRID 431408Notes

Reaction equation

HRID 431408 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:17][C@H:18]([C:23]([OH:25])=O)[CH2:19][CH:20]([CH3:22])[CH3:21].Cl.[CH3:27][NH:28][O:29][CH3:30].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2].[CH3:27][N:28]([O:29][CH3:30])[C:23](=[O:25])[C@H:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[NH2:17]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22879665HCID 22879665, compound

Product 1

HCID 131720343HCID 131720343, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-Boc-L-leucine-L-leucine (1 g), N,O-dimethylhydroxylamine hydrochloride (423 mg), 1-hydroxybenzotriazole monohydrate (509 mg), and N-methylmorpholine (0.42 mL) was dissolved in DMF (20 mL). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (610 mg) was added at 0° C. for 2 h, then at room temperature for 40 h. The reaction was quenched with water (80 mL) and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine then dried over anhydrous MgSO4, filtered, and evaporated to afford the product (923 mg) as a white solid.

Workup

  1. customThe reaction was quenched with water (80 mL)
  2. extractionthe mixture was extracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine
  4. dry with materialthen dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1405d419ef1a40e09687ae1480790eb8
Source dataset
uspto-grants-2003_12
Patent number
US06660268B1

Reaction notes

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