1,1-Dichloroethane → HCID 131718510, compound

HRID 1109552Notes

Reaction equation

HRID 1109552 reaction equation
ClC1C=[C:4]([CH:8]([OH:22])CN[C@H](C)CC2SC=C(C(O)=O)N=2)[CH:5]=[CH:6][CH:7]=1.[CH3:23][C:24]([CH3:36])([O:26][C:27]([NH:29][C@H:30]([CH3:35])[CH2:31][C:32](=[S:34])[NH2:33])=[O:28])[CH3:25].[OH-:37].[NH4+].Cl[CH:40](Cl)[CH3:41]>>[CH3:25][C:24]([CH3:36])([O:26][C:27]([NH:29][C@H:30]([CH3:35])[CH2:31][C:32]1[S:34][C:6]([CH2:5][CH2:4][C:8]([O:22][CH2:40][CH3:41])=[O:37])=[CH:7][N:33]=1)=[O:28])[CH3:23]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 14923Ammonium HydroxideHCID 9949853HCID 9949853, compoundHCID 53813132HCID 53813132, compound

Product 1

HCID 131718510HCID 131718510, compound

Procedure

A solution of crude title B compound (3.03 g, ~45% pure, ~6.1 mmol) and the title E compound of Example 1, (R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]butanethioamide (700 mg, 3.2 mmol), in dichloroethane (~40 mL) was refluxed under argon overnight. The dark brown reaction solution was poured into ice water (20 mL) which had been basified to pH 11-12 by addition of concentrated aq. ammonium hydroxide. The mixture was then extracted five times with methylene chloride (~40 mL), and the combined organic layers were dried over sodium sulfate. After concentration, the resulting brown oil was chromatographed on silica gel in 20% ethyl acetate/hexane to isolate the desired product as a brown oil (270 mg).

Workup

  1. extractionThe mixture was then extracted five times with methylene chloride (~40 mL)
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. concentrationAfter concentration
  4. customthe resulting brown oil was chromatographed on silica gel in 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-742f4e4362fc45b482002658c35e5734
Source dataset
uspto-grants-1994_06
Patent number
US05321036

Reaction notes

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