Ammonium → HCID 59750371, compound

HRID 748450Notes

Reaction equation

HRID 748450 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-06374d33c9a441658a5c707d707f8e48
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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