Triphenylphosphine → 3-(6-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

HRID 2089479Notes

Reaction equation

HRID 2089479 reaction equation
O[CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([NH:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:4][C:3]1=2.[NH:16]1[CH:20]=[C:19]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])[N:18]=[CH:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1>[CH:24]([O:23][C:21]([C:19]1[N:18]([CH:2]2[C:3]3[C:8](=[CH:7][C:6]([NH:12][C:13](=[O:15])[CH3:14])=[CH:5][CH:4]=3)[CH2:9][CH2:10][CH2:11]2)[CH:17]=[N:16][CH:20]=1)=[O:22])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 67546890N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamideHCID 178459416HCID 178459416, compound

Product 1

HCID 591993953-(6-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (0.553 g, 2.69 mmol) and isopropyl 4-imidazolecarboxylate (0.290 g, 1.88 mmol), which can be prepared as described in Example 1, in THF (10 mL) at 0° C. is added triphenylphosphine (1.415 g, 5.39 mmol) and dimethyl azodicarboxylate (40% wt. in toluene, 1.97 g, 5.39 mmol). The cooling bath is removed and the mixture is stirred for 15 min. Water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. The resulting residue is purified by silica gel chromatography (elution with dichloromethane-methanol mixtures) to give 3-(6-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 342.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.39 (d, J=6.3 Hz, 3 H), 1.40 (d, J=6.0 Hz, 3 H), 1.71-1.82 (m, 1 H), 1.83-1.92 (m, 1 H), 2.16 (s, 3H), 2.17-2.30 (m, 2 H), 2.86 (ddd, J=16.9, 8.3; 5.6 Hz, 1 H), 3.00 (dt, J=16.9, 5.6 Hz, 1 H), 5.25 (sept., J=6.3 Hz, 1 H), 6.30 (t, J=5.3 Hz, 1 H), 6.93 (d, J=8.3 Hz, 1 H), 7.34-7.36 (m, 2 H), 7.53 (d, J=1.8 Hz, 1 H), 7.74 (d, J=1.0 Hz, 1 H).

Workup

  1. customcan be prepared
  2. customThe cooling bath is removed
  3. additionWater is added
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography (elution with dichloromethane-methanol mixtures)

Sources & evidence

ORD record
ord-c23d6d5021124358a87c16501db46d6e
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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