4-Methylmorpholine → N-benzyloxy-2-[4-(4-bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methylbutyramide

HRID 2197272Notes

Reaction equation

[Br:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH:8]2[C:12](=[O:13])[N:11]([CH:14]([CH:18]([CH3:20])[CH3:19])[C:15]([OH:17])=O)[C:10](=[O:21])[NH:9]2)=[CH:4][CH:3]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:53]([O:60][NH2:61])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.Cl>CN(C=O)C>[CH2:53]([O:60][NH:61][C:15](=[O:17])[CH:14]([N:11]1[C:12](=[O:13])[CH:8]([CH2:7][O:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:23][CH:22]=2)[NH:9][C:10]1=[O:21])[CH:18]([CH3:20])[CH3:19])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of the compound obtained in step h above (22h) (300 mg, 0.782 mmol), NMM (0.19 mL, 1.72 mmol) and HOBt (179 mg, 1.329 mmol) in DMF (11 mL) were stirred at 0° C. for 10 minutes, then the reaction was cooled to −15° C., and EDCl (165 mg, 0.860 mmol) was added. The reaction was stirred for 30 minutes at −15° C. and then allowed to warm to room temperature, BnONH2HCl (137 mg, 0.860 mmol) was added. After being stirred overnight, the reaction mixture was concentrated under vacuum, and the residue was diluted with EtOAc and washed with brine. The combined organic layers were dried and concentrated; the residue was purified by silica gel column chromatography which gave the title compound as colorless oil (426 mg, 83% yield).

Workup

temperatureto warm to room temperature
stirringAfter being stirred overnight
concentrationthe reaction mixture was concentrated under vacuum
additionthe residue was diluted with EtOAc
washwashed with brine
customThe combined organic layers were dried
concentrationconcentrated
customthe residue was purified by silica gel column chromatography which

Sources & evidence

ORD record: ord-e80840d6a8e5434e92b4c09c8e3658c3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338471B2

Reaction notes

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