HCID 86602746, compound → HCID 86602745, compound

HRID 2054545Notes

Reaction equation

HRID 2054545 reaction equation
[C:1]1([C:7](=O)[S:8][C@@H:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:6]=[CH:5]C=CC=1>N.CO>[C:10]([C:9]1[S:8][C:6]([CH3:5])=[CH:1][C:7]=1[S:8][C@@H:9]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])#[N:11]

Participants

4

Reactant 1

HCID 86602746HCID 86602746, compound

Product 1

HCID 86602745HCID 86602745, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

S-[(1S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-phenylethyl] benzenecarbothioate (210 mg) was dissolved in 7M ammonia in methanol (10 ml) and stirred under nitrogen for 2 h. The solution was evaporated to dryness and the residue dissolved in dry DMF (10 ml). To this solution was added the product from step (a) (120 mg) followed by caesium carbonate (195 mg). The reaction mixture was stirred for 24 h, poured into water and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine and dried (MgSO4). The solvent was evaporated off and the residue purified by chromatography (silica, 20% ethyl acetate/isohexane as eluent) to give the sub-title compound as an oil (65 mg).

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in dry DMF (10 ml)
  3. additionTo this solution was added the product from step (a) (120 mg)
  4. stirringThe reaction mixture was stirred for 24 h
  5. additionpoured into water
  6. extractionextracted with ethyl acetate (3×50 ml)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated off
  10. customthe residue purified by chromatography (silica, 20% ethyl acetate/isohexane as eluent)

Sources & evidence

ORD record
ord-1623ae44aa4c488caff44e5914ece2d9
Source dataset
uspto-grants-2008_02
Patent number
US07329686B2

Reaction notes

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