Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 10233394 | HCID 10233394 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 20579062 | HCID 20579062 | 83.3% |
Reaction Steps
To a solution of N-(2S,4R)-[4-(3,4-dichlorobenzyl)-1-(methoxycarbonyl-methylcarbonyl)pyrrolidin-2-ylethyl]-2-[5-(3,4-dimethoxyphenyl)pyrimidin-2-ylsulfanyl]-acetamide (prepared according to Example 6 above) (40 mg, 0.06 mmol) in CH3OH was added 0.3 mL of a freshly prepared 1N aqueous solution of LiOH. The solution was stirred under N2 at 20° C. for 16 hrs, after which it was poured into water, the mixture then acidified with dilute aqueous H2SO4 and extracted with EtOAc. Drying and evaporation of the organic layer then afforded 33 mg of N-(2S,4R)-[4-(3,4-dichlorobenzyl)-1-(carboxymethylcarbonyl)pyrrolidin-2-ylethyl]-2-[5-(3,4-dimethoxyphenyl)pyrimidin-2-ylsulfanyl]acetamide (0.05 mmol) as a white amorphous foam, mass spectrum 647(MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06552028B2 |
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| Source dataset | uspto-grants-2003_04 |
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| ORD ID | ord-01d395c7ddc3452faf7d1f4e54783b26 |
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| Source note | uspto-grants-2003_04 |
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