Ethyl Acetate → HCID 178475072, compound

HRID 2277316Notes

Reaction equation

HRID 2277316 reaction equation
[C:1]([NH:4][C@@H:5]([CH3:24])[CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15](=[O:21])OC(C)(C)C)=[C:10]([OH:22])[C:9]=1[F:23])(=[O:3])[CH3:2].Cl.[C:26]([O:29][CH2:30][CH3:31])(=O)[CH3:27].C(O[CH2:36][CH3:37])(=O)C>>[C:1]([NH:4][C@@H:5]([CH3:24])[CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]([C:12]2[CH:11]=[CH:10][C:26]([O:29][CH2:30][C:31]3[CH:37]=[CH:36][CH:24]=[CH:5][CH:6]=3)=[CH:27][N:13]=2)=[O:21])=[C:10]([OH:22])[C:9]=1[F:23])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 178475073HCID 178475073, compound

Product 1

HCID 178475072HCID 178475072, compound

Procedure

A mixture of tert-butyl (6-(((2S)-2-acetamidopropyl)oxy)-5-fluoro-4-hydroxypyridin-3-yl)carbamate (453 mg), 4M hydrogen chloride/ethyl acetate (15 mL) and ethyl acetate (5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. Using the obtained residue and 5-(benzyloxy)pyridine-2-carboxylic acid, and in the same manner as in Step D of Example 83 and Step B of Example 123, the title compound was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d1e7260beed54dbbac2a4f870d2c8844
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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