Thioglycolic Acid → HCID 117697758, compound

HRID 1778524Notes

Reaction equation

HRID 1778524 reaction equation
[F:1][C:2]1([F:26])[CH:12]2[N:13](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH:8]([CH2:9][O:10][CH2:11]2)[C:7]2[CH:6]=[N:5]N[C:3]1=2.[Li+].[OH-].SCC(O)=[O:32]>CN(C=O)C>[F:1][C:2]1([F:26])[CH:12]2[NH:13][CH:8]([CH2:9][O:10][CH2:11]2)[C:7]2[CH:6]=[N:5][O:32][C:3]1=2

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 117697887HCID 117697887, compound

Product 1

HCID 117697758HCID 117697758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of compound 107e (100 mg, 0.26 mmol, 1.0 eq) and LiOH (33 mg, 0.78 mmol, 3.0 eq) in DMF (5 mL) was added mercaptoacetic acid (36 mg, 0.4 mmol, 1.5 eq) slowly, the mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo to give 7,7-difluoro-5,10-dioxa-4,12-diaza-tricyclo[6.3.1.0*2,6*]dodeca-2(6),3-diene 107a as an oil, used in next step without further purification. MS: calc'd (MH+) 202, measured (MH+) 202.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7896428e442f45a0a8005d789848fdbe
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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