Acetic-formic anhydride → Ethyl [(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(formyl)amino]acetate

HRID 1735890Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7]2.[CH:20](OC(=O)C)=[O:21]>C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:20]=[O:21])[CH2:7]2

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl [(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]acetate (7.15 g, 25.6 mmol) in 20 mL of methylene chloride under argon was cooled to approximately 0° C. Acetic formic anhydride (9.7 mL, 67.3 mmol) was cooled to 0° C. and added over 5 to 10 minutes. The mixture was stirred at 0° C. for 2 hours and then allowed to warm to room temperature. The solvent was removed by co-evaporation with toluene (3×50 mL). Crystallization of the residue under high vacuum gave ethyl [(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(formyl)amino]acetate (7.68 g, 25.0 mmol).

Workup

additionadded over 5 to 10 minutes
temperatureto warm to room temperature
customThe solvent was removed by co-evaporation with toluene (3×50 mL)
customCrystallization of the residue under high vacuum

Sources & evidence

ORD record: ord-832f957612fc4926852a5bae88f15aa2
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05538988

Reaction notes

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