Acetic Acid → 4-(2-Amino-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

HRID 2410641Notes

Reaction equation

HRID 2410641 reaction equation
[CH2:1]([O:8][C:9]1[CH:45]=[CH:44][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:31]C(OCC3C=CC=CC=3)=O)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][C:17]=2[O:42][CH3:43])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(O)=O>CO.[Pd]>[CH2:1]([O:8][C:9]1[CH:45]=[CH:44][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH2:31])[C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])=[CH:18][C:17]=2[O:42][CH3:43])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 585458034-(2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

Product 1

HCID 585456634-(2-Amino-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared using General Procedure 4: A solution of 4-(2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-3 (5.46 g, 8.81 mmol) and AcOH (5 mL) in MeOH (150 mL) was passed through the H-cube system with 10% Pd/C as a catalyst at 1 mL/min and 45° C. The reaction mixture was evaporated, dissolved in DCM (50 mL), and washed with saturated aqueous NaHCO3 (200 mL). The organic layer was dried over MgSO4 and concentrated to afford 3.93 g (92%) of 4-(2-amino-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-5. LCMS-ESI (m/z) calculated for C28H39NO6: 485. Found 430 [M+H-tBu]+, tR=2.15 min (Method 4). 1H NMR (400 MHz, DMSO) δ 8.06-7.99 (m, 2H), 7.12-7.05 (m, 3H), 7.02-6.98 (d, J=1.9 Hz, 1H), 6.85-6.78 (dd, J=8.1, 1.8 Hz, 1H), 4.11-4.03 (t, J=6.5 Hz, 2H), 3.71 (s, 3H), 3.51-3.45 (t, J=6.9 Hz, 1H), 2.87-2.73 (dt, J=16.9, 6.5 Hz, 2H), 1.91 (s, 2H), 1.79-1.69 (p, J=6.8 Hz, 2H), 1.47-1.23 (m, 17H), 0.90-0.83 (m, 3H).

Workup

  1. customPrepared
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in DCM (50 mL)
  4. washwashed with saturated aqueous NaHCO3 (200 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51b967149cef4e588936da001dbb44df
Source dataset
uspto-grants-2014_08
Patent number
US08816121B2

Reaction notes

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