Sodium Bicarbonate → HCID 11599255, compound

HRID 2222953Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:40])[C@@H:12]([N:23]2[C:27](=[O:28])[C:26]([C:30]3[CH:38]=[CH:37][C:33]4[O:34][CH2:35][O:36][C:32]=4[CH:31]=3)(O)[NH:25][C:24]2=[O:39])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[NH2:21])=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:40])[C@@H:12]([N:23]2[C:27](=[O:28])[CH:26]([C:30]3[CH:38]=[CH:37][C:33]4[O:34][CH2:35][O:36][C:32]=4[CH:31]=3)[NH:25][C:24]2=[O:39])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[NH2:21])=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 2-[(S)-2-(4-benzo[1,3]dioxol-5-yl4-hydroxy-2,5-dioxo-imidazolidin-1-yl)-3-(4-carbamoyl-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (80 mg, 0.14 mmol) in acetic acid (4.0 mL) was added zinc (183 mg, 2.8 mmol). The mixture was heated to 65° C. for 6 hours. The reaction was neutralized with saturated sodium bicarbonate at 0° C. and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvents were removed and the product was triturated with methanol/diethyl ether, filtered and dried to give 2-[(S)-2-(4-benzo[1,3]dioxol-5-yl-2,5-dioxo-imidazolidin-1-yl)-3-(4-carbamoyl-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (23 mg, 30%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customThe solvents were removed
customthe product was triturated with methanol/diethyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-83ac7fbabbae41a7bb4b3047de7733b8
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371869B2

Reaction notes

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