Water → HCID 58346341, compound

HRID 1941763Notes

Reaction equation

HRID 1941763 reaction equation
[F:1][C:2]1[C:3]([N+:21]([O-])=O)=[C:4]2[C:9]3=[C:10]([O:13][CH2:14][C@H:15]([CH3:16])[N:8]3[CH:7]=[C:6]([C:17]([NH2:19])=[O:18])[C:5]2=[O:20])[C:11]=1[F:12].S(S([O-])=O)([O-])=O.[Na+].[Na+].O>O.CO>[NH2:21][C:3]1[C:2]([F:1])=[C:11]([F:12])[C:10]2[O:13][CH2:14][C@H:15]([CH3:16])[N:8]3[C:9]=2[C:4]=1[C:5](=[O:20])[C:6]([C:17]([NH2:19])=[O:18])=[CH:7]3

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 58346345HCID 58346345, compound

Product 1

HCID 58346341HCID 58346341, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of 3 (1 g, 3.07 mmol) in a mixture of water/methanol (1:1 v/v, 30 mL) was added sodium hydrosulfite (Na2S2O4, 4.3 g, 24.6 mmol). The suspension was refluxed for 5 h until all starting material has disappeared. Upon completion, the reaction mixture was cooled to room temperature and 50 mL of water were added. After 20 minutes, a light yellow solid was collected by filtration and washed with water. The solid was dried under vacuo to give 4 (725 mg, 74% yield), which was used in the next step without further purification.

Workup

  1. temperatureThe suspension was refluxed for 5 h until all starting material
  2. filtrationa light yellow solid was collected by filtration
  3. washwashed with water
  4. customThe solid was dried under vacuo

Sources & evidence

ORD record
ord-623f14a212ec4d95a8a3249fd8ab1e8e
Source dataset
uspto-grants-2013_03
Patent number
US08389514B2

Reaction notes

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