Phosphorus pentachloride → 2-[(R)-2-(7-nitro-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

HRID 2089617Notes

Reaction equation

HRID 2089617 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][C@@H:5]([NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=1)[NH:25][C:24]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:23]2)=O)[CH2:6][S:7]CC1C=CC(OC)=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:38])[CH2:4][C@@H:5]1[CH2:6][S:7][C:18]([C:20]2[CH:21]=[C:22]3[C:26](=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=2)[NH:25][C:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:23]3)=[N:17]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 68477813(R)-4-(4-methoxy-benzylsulfanyl)-3-[(7-nitro-2-phenyl-1H-indole-5-carbonyl)-amino]-butyric acid methyl ester

Product 1

HCID 684764212-[(R)-2-(7-nitro-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl esterYield 60.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-4-(4-methoxy-benzylsulfanyl)-3-[(7-nitro-2-phenyl-1H-indole-5-carbonyl)-amino]-butyric acid methyl ester (533 mg, 1 mmol) prepared in Step A was dissolved in DCM (10 mL). Phosphorus pentachloride (406 mg, 2 mmol) was added thereto, and the mixture was stirred for 5 h at room temperature. The reaction was quenched by saturated aqueous sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The residue was purified by column chromatography to give the title compound (240 mg, Yield 60%).

Workup

  1. customThe reaction was quenched by saturated aqueous sodium bicarbonate solution
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationdistilled under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a39fac956884bc1bd2a2d037fa90668
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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