Thionyl Chloride → HCID 11152732, compound

HRID 499034Notes

Reaction equation

HRID 499034 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:23]([C:27]1[CH:31]=[C:30]([NH2:32])[O:29][N:28]=1)([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C>>[C:23]([C:27]1[CH:31]=[C:30]([NH:32][C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[O:29][N:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 810334-Benzyloxyphenylacetic acidHCID 81531DiisopropylethylamineHCID 20956943-Tert-butyl-1,2-oxazol-5-amine

Product 1

HCID 11152732HCID 11152732, compound

Conditions

Temperature
45 °C

Procedure

(4-Benzyloxy-phenyl)-acetic acid (50 mg, 0.2 mmol, 1 eq) was stirred with 1 mL of thionyl chloride at 80° C. for approximately three hours. The completion of the reaction was checked by TLC. Excess thionyl chloride was removed in vacuo, the residue was dissolved in dichloromethane and added to a mixture of 3-tert-butyl-isoxazol-5-ylamine (28 mg, 0.2 mmol, 1 eq) and DIEA (35 μL, 0.2 mmol, 1 eq). The reaction was stirred overnight at 45° C. The solvent was removed and the product purified by HPLC. Yield: 42 mg (57%), LC/MS [MH+] 365.

Workup

  1. customExcess thionyl chloride was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customThe solvent was removed
  4. customthe product purified by HPLC

Sources & evidence

ORD record
ord-09be2225863340c78e528612f8bb8a40
Source dataset
uspto-grants-2010_08
Patent number
US07767670B2

Reaction notes

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