4-Formylphenyl 4-(heptyloxy)benzoate → 4-(((2-(Tert-butoxy)-2-oxoethyl)amino)methyl)phenyl 4-(heptyloxy)benzoate

HRID 923552Notes

Reaction equation

HRID 923552 reaction equation
[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[NH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:18][CH:17]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 17122224-Formylphenyl 4-(heptyloxy)benzoateHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 892531264-(((2-(Tert-butoxy)-2-oxoethyl)amino)methyl)phenyl 4-(heptyloxy)benzoateYield 19%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Prepared using General Procedure 12: To a stirring solution of 4-formylphenyl 4-(heptyloxy)benzoate INT-12 (6.0 g, 17.6 mmol) in THF (30 mL) was added tert-butyl 2-aminoacetate hydrochloride (3.3 g, 19.7 mmol). After stirring for 2 h, sodium triacetoxyborohydride (7.5 g, 32.3 mmol) was added. After stirring for 12 h, the reaction mixture was diluted with NaHCO3 and the organic layer was separated. The remaining aqueous layer was extracted with DCM. The organic layers were combined, dried over Na2SO4, concentrated and purified by chromatography (EA/hexanes) to afford 155 mg (19%) of 4-(((2-(tert-butoxy)-2-oxoethyl)amino)methyl)phenyl 4-(heptyloxy)benzoate INT-13. LCMS-ESI (m/z) calculated for C27H37NO5: 455; found 456 [M+H]+, tR=3.27 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 8.18-8.09 (m, 2H), 7.41 (d, J=8.5 Hz, 2H), 7.18-7.08 (m, 2H), 7.01-6.88 (m, 2H), 4.08-3.98 (m, 2H), 3.78 (s, 2H), 3.23 (s, 2H), 1.89-1.75 (m, 2H), 1.55-1.41 (s, 9H), 1.45-1.21 (m, 6H), 1.15-1.06 (m, 2H), 0.88 (dd, J=8.5, 5.0 Hz, 3H).

Workup

  1. customPrepared
  2. stirringAfter stirring for 12 h
  3. customthe organic layer was separated
  4. extractionThe remaining aqueous layer was extracted with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-9d7da54ba12e44a7b6928f25bce8ca90
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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