HCID 54448554, compound → HCID 86754011, compound
Reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:8][S:9](=[O:24])(=[O:23])[CH2:10][CH2:11][NH:12]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2]>C(O)=O.CO.[Pd]>[CH:6]([OH:33])=[O:5].[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:8][S:9](=[O:23])(=[O:24])[CH2:10][CH2:11][NH2:12])([CH3:3])([CH3:4])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
t-Butyl-6-benzyloxycarbonylamino-2-t-butoxycarbonylamino-4,4-dioxo-4-thiahexanoate 152 mg) dissolved in 5% formic acid/methanol (8 ml) was added dropwise to a stirred suspension of 10% Pd/C in 5% formic acid/methanol (2 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 h then at room temperature for 1-2 h. The reaction mixture was filtered through hyflo, and the catalyst washed with methanol (25 ml) and water (25 ml). The filtrate was concentrated to one quarter volume in vacuo and diluted with water (25 ml). This process was repeated twice then evaporated to dryness in vacuo. The residue was dissolved in water and lyophilised to give an off-white solid (111 mg).
Workup
- waitat room temperature for 1-2 h
- filtrationThe reaction mixture was filtered through hyflo
- washthe catalyst washed with methanol (25 ml) and water (25 ml)
- concentrationThe filtrate was concentrated to one quarter volume in vacuo
- additiondiluted with water (25 ml)
- customThis process was repeated twice then evaporated to dryness in vacuo
- dissolutionThe residue was dissolved in water
Sources & evidence
- ORD record
- ord-4e9c8b42053a4e1bb6b9c80490bbf401
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05889056
Reaction notes
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