Acetic Acid → HCID 18947946, compound

HRID 1768504Notes

Reaction equation

HRID 1768504 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:20])([OH:19])[C:14](OCC)=[O:15])=[CH:9][CH:8]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].[C:39]1([NH:45][NH2:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O)(=O)C>C(Cl)Cl.C(OCC)C>[CH3:20][C:13]1([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]3[CH:21]=[CH:22][CH:23]=[CH:24][C:3]=3[Si:2]([CH3:1])([CH3:26])[CH3:25])=[CH:12][CH:11]=2)[O:19][C:27](=[O:28])[N:46]([NH:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:14]1=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 682631,1'-CarbonyldiimidazoleHCID 18947944HCID 18947944, compound

Product 1

HCID 18947946HCID 18947946, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2-(4-(2-trimethylsilylbenzyloxy)phenyl)lactate (0.93 g, 2.5 mmol) in CH2Cl2 (15 mL) was treated with 1,1'-carbonyldiimidazole (0.53 g, 3.3 mmol) and the resulting mixture was heated overnight. The resulting solution was diluted with diethyl ether (45 mL) and washed with H2O (two-times with 15 mL), brine (15 mL), dried (MgSO4) and concentrated under vacuum. The residue was dissolved in CH2Cl2 and to the solution was added PhNHNH2 (0.46 g, 4.3 mmol) and acetic acid (0.24 mL, 4.3 mmol). The resulting mixture was stirred at room temperature for 60 h afterwhich time the mixture was diluted with CH2Cl2 (20 ml) and washed with 1N aqueous HCl (10 mL) and H2O (10 mL). The organic phases were dried (MgSO4) and concentrated under vacuum to yield a residue which was subjected to column chromatography (75 g SiO2 eluted with 2:2:6 diethyl ether/CH2Cl2 /hexanes) thereby affording the product of Step E as a yellow powder, 0.62 g; (54%); m.p. 112°-114° C.; IR (mineral oil): 3308, 1738, 1245 cm-1 ; 1 H NMR (CDCl3): δ7.6 (d,1H), 7.55 (d,2H), 7.5 (d,1H), 7.45 (t,1H), 7.35 (t,1H), 7.25 (m,2h), 7.0 (d,3H), 6.75 (d,2H), 6.05 (s,1H), 5.1 (s,2h), 2.0 (s,3H), 1.23 (t,3H), 0.3 (s,9H).

Workup

  1. temperaturethe resulting mixture was heated overnight
  2. washwashed with H2O (two-times with 15 mL), brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in CH2Cl2 and to the solution
  6. washwashed with 1N aqueous HCl (10 mL) and H2O (10 mL)
  7. dry with materialThe organic phases were dried (MgSO4)
  8. concentrationconcentrated under vacuum
  9. customto yield a residue which
  10. washwas subjected to column chromatography (75 g SiO2 eluted with 2:2:6 diethyl ether/CH2Cl2 /hexanes)

Sources & evidence

ORD record
ord-4d04bf3211dd4865a6db6679f53030e9
Source dataset
uspto-grants-1995_01
Patent number
USH0001401

Reaction notes

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