Bromotrichloromethane → HCID 69201725, compound

HRID 2221439Notes

Reaction equation

HRID 2221439 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=2)=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)(Cl)(Cl)Br.C1CCN2C(=NCCC2)CC1>ClCCl>[C:1]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=2)=[CH:14][CH:15]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69200072HCID 69200072, compound

Product 1

HCID 69201725HCID 69201725, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-[4-(N-Boc-aminomethyl)-phenyl]4,5-dihydrooxazol-4-ylcarboxylate (25.5 g, 76.3 mmol) in dichloromethane (100 ml) was added CBrCl3 (8.23 ml, 83.9 mmol) and DBU (12.5 ml, 83.9 mmol). After stirring at room temperature overnight, the reaction was concentrated and the product isolated by flash chromatography over silica gel. Recrystallization from hot methanol provided methyl 2-[4-(N-Boc-aminomethyl)-phenyl]-oxazole-4-carboxylate (18.4 g, 55.4 mmol) as pale yellow crystals.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe product isolated by flash chromatography over silica gel
  3. customRecrystallization from hot methanol

Sources & evidence

ORD record
ord-ad3cd1ea78364c4397c02e1cbf03f069
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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