Stannous Chloride → HCID 68029006, compound

HRID 714140Notes

Reaction equation

HRID 714140 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:21][S:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[C:24]=1[N+:30]([O-])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[Sn](Cl)Cl>C1COCC1.O.C(Cl)Cl>[C:36]([O:35][C:34](=[O:40])[NH:33][C@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:21][S:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[C:24]=1[NH2:30])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 3

HCID 24479Stannous ChlorideHCID 517165Ammonium AcetateHCID 89930637HCID 89930637, compound

Product 1

HCID 68029006HCID 68029006, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl{(2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-[(3-nitro-2-oxo-1,2-dihydropyridin-4-yl)sulfanyl]propan-2-yl}carbamate (44, 507 mg, 0.87 mmol) and ammonium acetate (1.1 g, 14.0 mmol) in THF (12 ml) and water (3 ml) was treated with anhydrous tin(II) chloride (1.04 g, 5.5 mmol) and the mixture stirred at +65° C. for 22 h. The reaction mixture was diluted with DCM, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. Purification was performed in a chromatographic column on silicagel, eluted with 30% to 100% EtOAc in hexane to afford title compound (303 mg, 63% yield) as a light green solid. MS: m/z=576.2 (MNa+).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification
  6. washeluted with 30% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-fee541a7b6714044903dd368f5c4aa8d
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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