Stannous chloride dihydrate → HCID 57725359, compound

HRID 1091434Notes

Reaction equation

HRID 1091434 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@@H:7]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-])=O)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>C(O)C.[OH-].[Na+]>[C:1]([O:5][C:6](=[O:23])[C@@H:7]([NH:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[NH2:19])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 57725370HCID 57725370, compound

Product 1

HCID 57725359HCID 57725359, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of (S)-2-(5-chloro-2-nitro-benzoylamino)-butyric acid-tert-butyl ester (5.72 g,) in ethanol (250 ml) at ambient temperature was added tin(II) chloride bis-hydrate (18.8 g). The mixture was stirred at ambient for 16 hours. The volume was reduced to approximately 50 ml under reduced pressure, and reaction mixture was then diluted with 1M NaOH until the precipitate formed re-dissolved (400 ml). The aqueous was then extracted with diethyl ether (3×100 ml). The organic extracts were combined and washed with brine, dried (MgSO4), and concentrated to give the sub-titled compound as a yellow solid (4.60 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ 7.4 (1H, s), 7.2 (1H, d), 6.6 (2H, m), 5.5 (2H, m), 4.6 (1H, m), 2.0 (1H, m), 1.85 (1H, m), 1.5 (9H, s), 0.95 (3H, t) ppm.

Workup

  1. customThe volume was reduced to approximately 50 ml under reduced pressure, and reaction mixture
  2. customformed
  3. dissolutionre-dissolved (400 ml)
  4. extractionThe aqueous was then extracted with diethyl ether (3×100 ml)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd6424958ab44b17a72cd9b98133fc1d
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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