Water → HCID 20579062, compound

HRID 1267096Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:5][C@H:6]1[CH2:10][N:9]([C:11]([CH2:13][C:14]([O:16]C)=[O:15])=[O:12])[C@H:8]([CH2:18][CH2:19][NH:20][C:21](=[O:40])[CH2:22][S:23][C:24]2[N:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)=[CH:26][N:25]=2)[CH2:7]1.[Li+].[OH-].O.OS(O)(=O)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:5][C@H:6]1[CH2:10][N:9]([C:11]([CH2:13][C:14]([OH:16])=[O:15])=[O:12])[C@H:8]([CH2:18][CH2:19][NH:20][C:21](=[O:40])[CH2:22][S:23][C:24]2[N:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)=[CH:28][N:29]=2)[CH2:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

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+).

Workup

extractionextracted with EtOAc
customDrying
customevaporation of the organic layer

Sources & evidence

ORD record: ord-01d395c7ddc3452faf7d1f4e54783b26
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552028B2

Reaction notes

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