Phosphoric Acid → HCID 86749228, compound

HRID 375717Notes

Reaction equation

[C:1]([O:4][C:5]1[C:6]([CH3:45])=[C:7]([C:16]([CH2:23][S:24][CH2:25][C@H:26]([NH:31][C:32](=[O:44])[C@@H:33]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][OH:35])[C:27]([O:29][CH3:30])=[O:28])=[C:17]([O:19][C:20](=[O:22])[CH3:21])[CH:18]=1)[C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])(=[O:3])[CH3:2].P(=O)(O)(O)O.P([O-])(O)(O)=O.[Na+]>[Zn].O1CCCC1>[C:1]([O:4][C:5]1[C:6]([CH3:45])=[C:7]([C:16]([CH2:23][S:24][CH2:25][C@H:26]([NH:31][C:32](=[O:44])[C@@H:33]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][OH:35])[C:27]([O:29][CH3:30])=[O:28])=[C:17]([O:19][C:20](=[O:22])[CH3:21])[CH:18]=1)[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 1.90 g of 2,2,2-trichloroethyl 3,5-diacetoxy-6-[[((R)-2-[(S)-2-(1-t-butoxyformamido)-3-hydroxypropionamido]-2-(methoxycarbonyl)ethyl]thio]methyl]-2-methylbenzoate, 50 ml of tetrahydrofuran, 12.5 ml of 1M phosphoric acid, 12.5 ml of 1M aqueous sodium dihydrogen phosphate solution and 3.2 g of zinc powder was stirred at 20° C. for 1.2 hours. The mixture was filtered, and the unsoluble material was washed with water and ethyl acetate. The filtrate was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and evaporated in vacuo to afford 3,5-diacetoxy-6-[[[(R)-2-((S)-2-(1-t-butoxyformamido)-3-hydroxypropionamido]-2-(methoxycarbonyl)ethyl]thio]methyl]-2-methylbenzoic acid as a solidifying oil.

Workup

filtrationThe mixture was filtered
washthe unsoluble material was washed with water and ethyl acetate
customThe filtrate was partitioned between ethyl acetate and water
dry with materialThe organic layer was dried over sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-7a2e8e5724f349b9b8cc4ac09937b9eb
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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