Phosphorus pentachloride → 2,2-dimethyl-propionic acid (R)-2-(7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-ylmethyl ester

HRID 1515255Notes

Reaction equation

HRID 1515255 reaction equation
COC1C=CC(C[S:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]2[NH:23][C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][C:25]=3[N+:31]([O-:33])=[O:32])=O)[CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl>[N+:31]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[NH:23][C:22]([C:20]1[S:8][CH2:9][C@@H:10]([CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[N:19]=1)=[CH:30]2)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 595430732,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzylsulfanyl)-2-[(7-nitro-1H-indole-2-carbonyl)-amino]-propyl ester

Product 1

HCID 595431172,2-dimethyl-propionic acid (R)-2-(7-nitro-1H-indol-2-yl)-4,5-dihydro-thiazol-4-ylmethyl esterYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzylsulfanyl)-2-[(7-nitro-1H-indole-2-carbonyl)-amino]-propyl ester (1.6 g, 3.2 mmol) prepared in Step B was dissolved in dichloromethane (50 mL). Phosphorus pentachloride (1.3 g, 6.4 mmol) was added thereto, and the mixture was stirred for 5 h at room temperature. Saturated aqueous sodium bicarbonate solution was added to the mixture to quench the reaction. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The residue was purified by column chromatography to give the title compound (0.8 g, Yield 69%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-892e70be48c640488d7503bf543a6547
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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