Stannous Chloride → HCID 68818292, compound

HRID 900363Notes

Reaction equation

HRID 900363 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.[Sn](Cl)Cl>CO.ClCCl>[CH3:1][O:2][C:3](=[O:25])[C@@H:4]([NH:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68820728(2R)-methyl-2-tert-butoxycarbonylamino-3-(4-nitro-benzylsulfanyl)-propionate

Product 1

HCID 68818292HCID 68818292, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2R)-methyl-2-tert-butoxycarbonylamino-3-(4-nitro-benzylsulfanyl)-propionate (3.75 g, 10.1 mmol) and tin (II) chloride (5.76 g, 30.0 mmol) in methanol (50 mL) was stirred at 50° C. Upon completion (TLC: 5% methanol in dichloromethane), the mixture was cooled to room temperature, quenched with saturated potassium fluoride solution (75 mL) and extracted with diethyl ether (3×75 mL). The combined extract was washed sequentially with water and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Flash chromatography purification (SiO2; 1-2% methanol in dichloromethane as eluent) yielded the titled compound as an off-white solid. 1H NMR (CDCl3, 300 MHz) δ 7.08 (2H, d, J=8 Hz, ArH), 6.25 (2H, d, J=8 Hz, ArH), 4.53 (1H, m, CHN), 3.75 (3H, s, OCH3), 3.63 (2H, s, PhCH2S), 2.84 (2H, m, CH2CHN), 1.46 (9H, s, CMe3); ESI-LCMS e/z calculated for C16H24N2O4S 340.146. found 341 (M+H)+, 363 (M+Na)+.

Workup

  1. customquenched with saturated potassium fluoride solution (75 mL)
  2. extractionextracted with diethyl ether (3×75 mL)
  3. extractionThe combined extract
  4. washwas washed sequentially with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customFlash chromatography purification (SiO2; 1-2% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-5d6084b1f1154ddeb4c5cbc8c4ca677b
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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