Ammonium → HCID 59750371, compound

HRID 499632Notes

Reaction equation

HRID 499632 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:14][CH:13]=2)=[N:3]1.ClC(OCC(C)C)=O.C([N:33](CC)CC)C.[NH4+]>C1COCC1>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([NH2:33])=[O:22])=[CH:14][CH:13]=2)=[N:3]1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 59750456HCID 59750456, compound

Product 1

HCID 59750371HCID 59750371, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-3-pyridyl]propionic acid (0.31 g, 1.00 mmol), isobutyl chloroformate (0.22 ml, 1.50 mmol) and triethylamine (0.22 ml, 1.50 mmol) were dissolved in THF (10 ml), and the mixture was stirred under ice cooling condition for 1 hr. 25% aqueous ammonium solution was added to the mixture, and the mixture was stirred under ice cooling condition for 0.5 hr. The obtained precipitates were recrystallized from ethanol to give the titled compound (0.17 g, 55%) as white crystals.

Workup

  1. stirringthe mixture was stirred under ice cooling condition for 0.5 hr
  2. customThe obtained precipitates
  3. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-6862bf27001c4b49b8aabe8b18319d1c
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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