2-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methyl-butyric acid methyl ester → HCID 66660886, compound

HRID 2197271Notes

Reaction equation

HRID 2197271 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([NH:8][C:9](=[O:28])[CH:10]([NH:20][C:21](OC(C)(C)C)=[O:22])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)[CH:5]([CH3:7])[CH3:6].COC(=O)C(N1C(=O)C(COC2C=CC(Br)=CC=2)NC1=O)C(C)C>Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH:10]2[C:9](=[O:28])[N:8]([CH:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:2])=[O:29])[C:21](=[O:22])[NH:20]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 666606712-[4-(4-Bromophenoxymethyl)-2,5-dioxo-imidazolidin-1-yl]-3-methyl-butyric acid methyl esterHCID 666609032-[3-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

Product 1

HCID 66660886HCID 66660886, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the compound obtained in step g above (22g) (759 mg, 1.907 mmol) and 3 N HCl (20 mL) was stirred at 80° C. for 2 h. The reaction mixture was cooled down and then extracted with EtOAc. The combined organic layers were dried and concentrated; the crude product was purified by silica gel column chromatography which gave the title compound as colorless oil (300 mg, 41%).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe crude product was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-98db85b568764f85b90ed13c5b86b72e
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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