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Benzyl Bromide → [(2-Benzyloxy-phenyl)-tert-butoxycarbonylmethyl-amino]-acetic acid tert-butyl ester

HRID 2357126
Notes
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Reaction equation

HRID 2357126 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86596786[tert-Butoxycarbonylmethyl-(2-hydroxy-phenyl)-amino]-acetic acid tert-butyl ester

Product 1

HCID 68637211[(2-Benzyloxy-phenyl)-tert-butoxycarbonylmethyl-amino]-acetic acid tert-butyl esterYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of [tert-Butoxycarbonylmethyl-(2-hydroxy-phenyl)-amino]-acetic acid tert-butyl ester (11) (7.4 g, 21.9 mmol) in dry THF (50 mL) was treated with sodium hydride (0.81 g, 33.8 mmol) at 0° C. under an Ar atmosphere. After stirring at 0° C. for 30 min, benzyl bromide (3.9 mL, 32.7 mmol) was added. The mixture was stirred at 0° C. for another 30 min and then warmed to room temperature overnight. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with CH2Cl2/hexane/EtOAc=1:4:0.2 to yield 6.3 g (67%) of the desired product 12 as a colorless oil. Rf=0.33 (in CH2Cl2/hexane/EtOAc=1:4:0.2); 1H NMR (300 MHz, CDCl3) δ 7.45-7.28 (m, 5H), 6.84 (m, 4H), 5.12 (s, 2H), 4.08 (s, 4H), 1.40 (s, 18H); 13C NMR (75 MHz, CDCl3) δ 170.5, 150.5, 139.6, 137.5, 128.4, 127.6, 127.2, 121.9, 121.4, 119.4, 114.7, 81.0, 70.9, 54.6, 28.0; mass spectrum, calculated for C25H33NO5 (MH+) 428.2, Found 427.9.

Workup

  1. stirringThe mixture was stirred at 0° C. for another 30 min
  2. temperaturewarmed to room temperature overnight
  3. customThe reaction mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash column chromatography
  9. washeluting with CH2Cl2/hexane/EtOAc=1:4:0.2

Sources & evidence

ORD record
ord-22cf8cf466734fdbbdb1d212107ebac7
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759459B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes