Phosphorus oxychloride → HCID 71269501, compound

HRID 1429392Notes

Reaction equation

HRID 1429392 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[CH2:7][C@H:8]1[N:15]([S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[CH:24]3)(=[O:18])=[O:17])[CH2:14][C:13]2[CH:29]=[CH:30][CH:31]=[CH:32][C:12]=2[CH2:11][O:10][CH2:9]1)(=[O:3])[CH3:2].O=P(Cl)(Cl)Cl>O>[CH3:2][C:1]1[O:3][C:6]([CH2:7][C@H:8]2[N:15]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)(=[O:18])=[O:17])[CH2:14][C:13]3[CH:29]=[CH:30][CH:31]=[CH:32][C:12]=3[CH2:11][O:10][CH2:9]2)=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 71269539HCID 71269539, compound

Product 1

HCID 71269501HCID 71269501, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of compound 27a (100 mg, 0.21 mmol) and POCl3 (3 mL) was stirred at 110° C. for 3 h. The mixture was taken up in H2O (10 mL) and extracted with DCM (30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by Prep-TLC to give the pure compound 27 (40 mg, 42% yield). LCMS (m/z): 451.1 (MH+).

Workup

  1. extractionextracted with DCM (30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by Prep-TLC

Sources & evidence

ORD record
ord-612557b7f0de447cb2e6f4a5f36727c6
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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