1,1-Dimethylethyl (2E,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(phenylthio)-2-pentenoate → HCID 11638423, compound
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].C1(C)C=CC=CC=1>[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
4
Procedure
A mixture of Example 480A (5 g, 13.2 mmol) and Wilkinson's catalyst (1 g) in toluene (125 mL) was stirred under H2 at 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 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
- temperaturecooled
- filtrationfiltered through silica gel
- concentrationconcentrated
- dissolutionThe concentrate was dissolved in 3:1:1 THF/water/MeOH (150 mL)
- additiontreated with a 10-fold excess of LiOH
- additionThe mixture was poured into saturated NaH2PO4 (200 mL)
- extractionextracted three times with ethyl acetate (200 mL)
- washThe combined extracts were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d87b8e9fb5e64a65bf8e690bcad92454
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754886B2
Reaction notes
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