Propylamine → HCID 86653783, compound

HRID 1528138Notes

Reaction equation

HRID 1528138 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28]C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([N:39]1[CH:43]=[CH:42]N=C1)(N1C=CN=C1)=[O:33].[CH2:44](N)CC>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][C:32]([NH:39][CH2:43][CH2:42][CH3:44])=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7852PropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 86653782HCID 86653782, compound

Product 1

HCID 86653783HCID 86653783, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanoic acid (325 mg) in 3 mL THF was treated with carbonyldiimidazole (177 mg, 1.06 mmol). The cloudy yellow solution was stirred at room temperature for 1.5 h. One portion of ˜0.45 mmol was added to a solution of n-propylamine (155 μL, 111 mg) in 2 mL THF and let stir overnight. The reaction mixture was concentrated to a pink-tan solid, dissolved into 5 mL CH2Cl2 and washed with 1×3 mL 2.5 M HCl, 1×3 mL saturated aqueous NaHCO3, 2×2 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to yield 117 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-N-propylbutanamide as a white powder. MS M++H at 460 m/z; 1H NMR (400 MHz, CDCl3) δ=7.50 (m, 4H), 7.44-7.35 (m, 6H), 5.47 (br m, 1H), 4.74 (s, 2H), 4.73 (s, 2H), 3.03 (q, 2H), 2.70 (t, 2H), 2.27 (s, 3H), 2.25 (s, 3H), 2.23 (s, 3H), 2.14 (t, 2H), 1.84 (pent, 2H), 1.39 (m, 2H), 0.84 (t, 3H) ppm.

Workup

  1. stirringlet stir overnight
  2. concentrationThe reaction mixture was concentrated to a pink-tan solid
  3. dissolutiondissolved into 5 mL CH2Cl2
  4. washwashed with 1×3 mL 2.5 M HCl, 1×3 mL saturated aqueous NaHCO3, 2×2 mL saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b6949ed4689c4cfc910283f76554f2ca
Source dataset
uspto-grants-2015_07
Patent number
US09090576B2

Reaction notes

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