Butyl Formate → HCID 53685709, compound

HRID 863072Notes

Reaction equation

HRID 863072 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][C@H:6]([NH:13][CH2:14][C:15]#[N:16])[CH2:7]2.[CH:17](OCCCC)=[O:18]>>[C:15]([CH2:14][N:13]([C@H:6]1[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=2[F:1])[CH2:7]1)[CH:17]=[O:18])#[N:16]

Participants

3

Reactant 2

HCID 11614Butyl FormateHCID 54324822HCID 54324822, compound

Product 1

HCID 53685709HCID 53685709, compound

Procedure

A solution of the (S)-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamino)acetonitrile in butyl formate (8.7M, 240 mL, 2.10 mol) was heated to reflux and stirred under nitrogen for 19 hours. The solvents were removed under reduced pressure, toluene was added and then evaporated. Drying gave (S)-N-(cyanomethyl)-N-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)formamide as an oily residue (53.2 g). A stirring mixture of the formamide (53.2 g) and ethyl formate (12.4M, 48.7 mL, 0.604 mol) in 0.925 L of anhydrous THF was cooled to -15° C. A solution of potassium tert-butoxide in THF (1.0M, 302 mL, 0.302 mol) was added over 20 minutes and the mixture was stirred for 18 hours. Evaporation of the solvent gave potassium (S)-N-(1-cyano-2-oxyvinyl)-N-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)formamide as a residue.

Workup

  1. temperatureto reflux
  2. customThe solvents were removed under reduced pressure, toluene
  3. additionwas added
  4. customevaporated
  5. customDrying

Sources & evidence

ORD record
ord-dbb0dca0154f44b4bc4be9681e100f32
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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