4-Methylmorpholine → HCID 86612118, compound

HRID 2114838Notes

Reaction equation

HRID 2114838 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][N:19](C)[OH:20].[CH3:22]N1CCOCC1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CCOC(C)=O>[CH3:22][O:20][N:19]([CH3:18])[C:14]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:16]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acid

Product 1

HCID 86612118HCID 86612118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[(tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (5.89 g, 25.68 mmol) in CH2Cl2 (25 mL) were added dimethylhydroxylamine hydrochloride (2.51 g, 25.68 mmol) and N-methylmorpholine (2.82 mL, 25.68 mmol), sequentially. The mixture was cooled to 0° C., treated with 1.0M DCC in CH2Cl2, and stirred under an atmosphere of nitrogen while warning to room temperature overnight. The mixture was filtered, washing with CH2Cl2, and the resulting filtrate was concentrated in vacuo to afford an oil. The oil was re-suspended in EtOAc, and the mixture was filtered once more. The resulting filtered was subjected to column chromatography eluting with a gradient of 0-100% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product as an opaque white solid.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with CH2Cl2
  3. concentrationthe resulting filtrate was concentrated in vacuo
  4. customto afford an oil
  5. filtrationthe mixture was filtered once more
  6. filtrationThe resulting filtered
  7. washeluting with a gradient of 0-100% EtOAc/hexanes
  8. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-d2d0f5122ffa498a8557e1b4cdb9ae4e
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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