Acetic Acid → HCID 68433506, compound

HRID 2243813Notes

Reaction equation

HRID 2243813 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:31])([C:27]([O:29][CH3:30])=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19](=O)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:36]([NH:43][CH:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:18][O:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][C@@:9]([CH3:31])([C:27]([O:29][CH3:30])=[O:28])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 176Acetic Acid3×HCID 7504Benzylamine3×HCID 5049666Sodium triacetoxyborohydride3×HCID 68433687HCID 68433687, compound

Product 1

HCID 68433506HCID 68433506, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl N-(tert-butoxycarbonyl)-alpha-methyl-3-(2-oxo-2-phenylethoxy)phenylalaninate (0.600 g, 1.40 mmol), 4 A sieves (spatula tip), acetic acid (0.089 mL, 1.54 mmol), and benzylamine (0.184 mL, 1.68 mmol) in 10.0 mL dichloroethane was added sodium triacetoxyborohydride (0.357 g, 1.68 mmol). After 16 hr, additional benzylamine (0.092 mL, 0.840 mmol), sodium triacetoxyborohydride (0.178 g, 0.840 mmol), and acetic acid (0.045 mL, 0.770 mmol) were added. After an additional 16 hr, the temperature was raised to 50° C. for 30 hr., and additional amounts of 4 A sieves, acetic acid, benzylamine, and sodium triacetoxyborohydride were added over 72 hr to achieve full conversion. The reaction was quenched with bicarb. and filtered, washing with water and EtOAc. The layers of the filtrate were separated, and the aqueous layer was back extracted with EtOAc. The organic layers were combined, washed with bicarb. and brine (×2), dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography (90 g silica, 0-30% EtOAc in hexanes) gave methyl 3-[2-(benzylamino)-2-phenylethoxy]-N-(tert-butoxycarbonyl)-alpha-methylphenylalaninate as a yellow foam.

Workup

  1. waitAfter an additional 16 hr
  2. customThe reaction was quenched with bicarb
  3. filtrationand filtered
  4. washwashing with water and EtOAc
  5. customThe layers of the filtrate were separated
  6. extractionthe aqueous layer was back extracted with EtOAc
  7. washwashed with bicarb
  8. dry with materialand brine (×2), dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography (90 g silica, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f86d2983cae94c55b6ffbcf5b6aeadac
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

Loading…