Benzyl Bromide → Benzyl 3-(3-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

HRID 2403244Notes

Reaction equation

HRID 2403244 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC(C)=O>[CH2:34]([O:27][C:23]1[CH:22]=[C:21]([CH2:20][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:26]=[CH:25][CH:24]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71209119Benzyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate

Product 1

HCID 22623796Benzyl 3-(3-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoateYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

171 (580 mg, 1 equivalent) was dissolved in 15 ml of acetone, then potassium carbonate (238 mg, 1.1 equivalent) and benzylbromide (1.1 equivalent, 206 μl) were added successively. The reaction mixture was let overnight at room temperature. The reaction mixture is concentrated and 50 ml of AcOEt are added. The organic phase are washed with 10% citric acid, saturated NaHCO3 and brine then dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (AcOEt/Hexane 2/8) to afford 172 as white solid (513 mg, 71%). 1H NMR (CDCl3): δ 1.46 (s, 9H), 2.64 (s, 1H), 3.05 (m, 1H), 3.18 (m, 1H), 4.39 (m, 1H), 5.20 (s, 1H), 5.25 (s, 4H), 6.95 (d, 1H, J=7.1 Hz), 7.00 (d, 1H, J=7.9 Hz), 7.07 (s, 1H), 7.20 (m, 2H), 7.27 (d, 2H, J=7.4 Hz), 7.32 (t, 1H, J=7.9 Hz), 7.50 (m, 6H).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition50 ml of AcOEt are added
  3. washThe organic phase are washed with 10% citric acid, saturated NaHCO3 and brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (AcOEt/Hexane 2/8)

Sources & evidence

ORD record
ord-a164d065c7be4734bebbead319f1c200
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

Loading…