Thionyl Chloride → HCID 22255777, compound

HRID 1182436Notes

Reaction equation

HRID 1182436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([OH:23])=O)[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([Cl:26])=[O:23])[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 9933119HCID 9933119, compound

Product 1

HCID 22255777HCID 22255777, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,5-Dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetic acid (444 mg) was mixed with 10 ml thionyl chloride and heated at reflux for 3 h. The reaction mixture was co-evaporated with toluene to give the crude 3,5-dibromo-4-(4-hydroxy-3-isopropyl-phenoxy)phenylacetyl chloride. N,O-bis(trimethylsilyl)acetamide (670 mg) was added at 0° C., under nitrogen atmosphere, to a mixture of D-Aspargine (225 mg) and 10 ml acetonitrile. The reaction mixture was further stirred at room temperature and a solution of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetyl chloride in 10 ml acetonitrile was added. After stirring for 16 h, the reaction mixture was poured into water and the solid filtered off. The solid was dissolved in methanol and the organic phase removed in vacuo. The residue was purified by HPLC to give 76 mg (14%) of D-N-[3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)phenylacetyl]aspargine. LC-MS (electrospray): m/z 557 (M−H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-8462e5785b864033a836d654640bbd96
Source dataset
uspto-grants-2007_10
Patent number
US07288571B2

Reaction notes

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