Hydrochloric Acid → HCID 69655224, compound

HRID 985763Notes

Reaction equation

HRID 985763 reaction equation
[NH2:1][C@H:2](C(O)=O)[CH2:3]C1C=C2C(C=CC=C2)=CC=1.[F:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][CH2:24][C:25]2=O)=[CH:20][CH:19]=1.Cl>C1COCC1>[F:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][CH2:24][C:25]2=[CH:3][C:2]#[N:1])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1859152-NaphthylalanineHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 69655224HCID 69655224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1.6 eq. of Nal are suspended in 130 ml of anhydrous THF under a nitrogen atmosphere in a 250 ml three-necked flask. The mixture is cooled in a bath of ice/salt and 1.6 eq. of diethyl cyanomethylenephosphonate in 40 ml of THF are added dropwise. The reaction mixture is stirred for 45 minutes and then, whilst still cold, 1 eq. of the compound obtained in Step E, in 70 ml of THF, is added dropwise. The mixture is stirred for 4 hours and is then poured onto a mixture of ice/water, acidified with 3M HCl solution and extracted 3 times with ethyl ether. The organic phase is dried over MgSO4 and evaporated under reduced pressure; the residue obtained is recrystallised.

Workup

  1. additionare added dropwise
  2. stirringThe mixture is stirred for 4 hours
  3. extractionextracted 3 times with ethyl ether
  4. dry with materialThe organic phase is dried over MgSO4
  5. customevaporated under reduced pressure
  6. customthe residue obtained
  7. customis recrystallised

Sources & evidence

ORD record
ord-dccd99f87e0247069be7b8d6d9ceaf81
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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