4-Methylmorpholine → HCID 53999817, compound

HRID 727558Notes

Reaction equation

HRID 727558 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:13][N:14]1[C:18]([CH2:23][CH:24]([CH3:26])[CH3:25])([CH2:19][C:20](O)=[O:21])[C:17](=[O:27])[N:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:15]1=[O:36].Cl.[CH2:38]([O:45][NH2:46])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CN1CCOCC1>C(Cl)Cl>[CH2:38]([O:45][NH:46][C:20](=[O:21])[CH2:19][C:18]1([CH2:23][CH:24]([CH3:25])[CH3:26])[C:17](=[O:27])[N:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:15](=[O:36])[N:14]1[CH3:13])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 19705554HCID 19705554, compound

Product 1

HCID 53999817HCID 53999817, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CDI (57.0 mg, 0.352 mmol) is added to a solution of 3-methyl-4-(2-methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-4-imidazolidineacetic acid (113 mg, 0.340 mmol) and CH2Cl2 (2.5 mL). The solution is stirred for 1 hour at room temperature and then O-benzyl hydroxylaminehydrochloride (67.0 mg, 0.420 mmol) and N-methylmorpholine (46 μL, 0.42 mmol) are added. The solution is stirred for 60 hours at room temperature. Basic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc) provides 94.8 mg (64%) of the title compound as a white solid.

Workup

  1. stirringThe solution is stirred for 60 hours at room temperature
  2. customBasic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-8c0b9cd570a64c30acdbf86655d12668
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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