Ammonium Chloride → HCID 15855304, compound

HRID 654307Notes

Reaction equation

HRID 654307 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:10](OS(C)(=O)=O)/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>O1CCCC1>[CH2:22]([C@H:12](/[CH:11]=[CH:10]/[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]([O:15][CH3:16])=[O:14])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 14656853HCID 14656853, compound

Product 1

HCID 15855304HCID 15855304, compoundYield 167.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Cuprous cyanide (5 mg) was placed in a flask which was flushed with N2 gas. Anhydrous tetrahydrofuran (0.5 ml) was added, and the mixture was cooled under N2 to 30° C. A solution of benzylmagnesium chloride (0.18 ml, 1.0M in diethyl ether) was added, and the mixture was stirred for 10 min to produce a yellow slurry. A solution of 30 mg (0.073 mmol) of the resultant compound of Example 7 in 1 ml of anhydrous tetrahydrofuran was subsequently added, and the resulting solution was stirred and allowed to warm to -10° C. over a period of 30 min. After addition of aqueous ammonium chloride, the mixture was extracted with ethyl acetate, washed with saturated brine, dried over Na2SO4, and concentrated in vacuo. Chromatography on silica gel using 6:1 hexane:ethyl acetate provided 25 mg (84%) of the desired compound (Rf 0.71, 2:1 hexane:ethyl acetate). 1H NMR (CDCl3) δ 1.41 (s, 9 H), 2.2-2.3 (m, 3 H), 3.04 (dd, J=13, 7 Hz, 1 H), 3.25 (q, J=7 Hz, 1 H), 3.61 (s, 3 H), 4.37 (m, 2 H), 5.39 (dd, J=15, 5 Hz, 1 H), 5.55 (dd, J=15, 8 Hz, 1 H), 7.05-7.15 (m, 4 H), 7.2-7.3 (m, 6 H). Mass spectrum: (M+NH4)+ =427.

Workup

  1. customwhich was flushed with N2 gas
  2. additionAnhydrous tetrahydrofuran (0.5 ml) was added
  3. additionA solution of benzylmagnesium chloride (0.18 ml, 1.0M in diethyl ether) was added
  4. customto produce a yellow slurry
  5. stirringthe resulting solution was stirred
  6. temperatureto warm to -10° C. over a period of 30 min
  7. extractionthe mixture was extracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6caf36566ac04d748f8591a0b56b40c4
Source dataset
uspto-grants-1992_07
Patent number
US05130468

Reaction notes

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