1,1-Dimethylethyl (2E,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(phenylthio)-2-pentenoate → HCID 11638423, compound

HRID 1785850Notes

Reaction equation

HRID 1785850 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:19][S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[CH:10]=[CH:11]/[C:12]([O:14]C(C)(C)C)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:19][S:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 116965641,1-Dimethylethyl (2E,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(phenylthio)-2-pentenoate

Product 1

HCID 11638423HCID 11638423, compound

Reagents, catalysts & solvents 1

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst

Procedure

A mixture of Example 480A (5 g, 13.2 mmol) and Wilkinson's catalyst (1 g) in tolune (125 mL) was stirred under H2at 60° C. for 18 hours, cooled, filtered through silica gel, and concentrated. The concentrate was dissolved in 3:1:1 THF/water/MeOH (150 mL), treated with with a 10-fold excess of LiOH, and stirred for 24 hrs. The mixture was poured into saturated NaH2PO4 (200 mL) and extracted three times with ethyl acetate (200 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 324, 326 (M−H)−, (M+H)+.

Workup

  1. temperaturecooled
  2. filtrationfiltered through silica gel
  3. concentrationconcentrated
  4. dissolutionThe concentrate was dissolved in 3:1:1 THF/water/MeOH (150 mL)
  5. additiontreated with with a 10-fold excess of LiOH
  6. additionThe mixture was poured into saturated NaH2PO4 (200 mL)
  7. extractionextracted three times with ethyl acetate (200 mL)
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-244e338b6ba5467ab1f9666d165202d8
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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