Methanol → HCID 59486028, compound

HRID 1972291Notes

Reaction equation

HRID 1972291 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:26])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.CO.O>C(Cl)Cl>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:26])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 45480480HCID 45480480, compound

Product 1

HCID 59486028HCID 59486028, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (S)-1-(4-(4-chlorophenoxy)phenyl)-5-(3-methoxyphenyl)-imidazolidin-2-one (99 mg, 0.25 mmol) in CH2Cl2 (2 mL) is cooled to −78° C. when BBr3 (1 mmol, 1 mL of 1M solution in CH2Cl2) is added drop wise. After the addition, the mixture is warmed to 0° C. and stirred for 1 h when MeOH (0.5 mL) is added into the mixture to quench the reaction. The reaction mixture is then treated with water (3 mL) and extracted with EtOAc (3×5 mL). The combined organic layers are concentrated and purified by flash column chromatography (silica gel, 0-100% EtOAc/hexane) to provide the titled compound as a white solid (84 mg, 88%). HPLC-MS calculated for C21H17ClN2O3 (M+H+) 381.1, found 381.1.

Workup

  1. additionis added drop wise
  2. additionAfter the addition
  3. additionis added into the mixture
  4. customto quench
  5. customthe reaction
  6. extractionextracted with EtOAc (3×5 mL)
  7. concentrationThe combined organic layers are concentrated
  8. custompurified by flash column chromatography (silica gel, 0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-a0d595a5a6ad4d59a8917d13db87a143
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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