Water → (S)-(4-Benzyloxy-phenyl)-tert-butoxycarbonylamino-acetic acid benzyl ester

HRID 1009965Notes

Reaction equation

HRID 1009965 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[CH2:26]([O:11][C:10](=[O:12])[C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:15][CH:14]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11300124(S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

Product 1

HCID 57994316(S)-(4-Benzyloxy-phenyl)-tert-butoxycarbonylamino-acetic acid benzyl esterYield 184%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-tert-butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (32.03 g, 120 mmol) in DMF (300 ml) was added potassium carbonate (35 g, 252 mmol) and benzylbromide (30 ml, 252 mmol). The reaction mixture was stirred at 50° C. under a nitrogen atmosphere for 17 h. The mixture was poured into water (1l) and extracted with EtOAc (3×600 ml). The combined organic extracts were washed with water (3×600 ml), brine (600 ml), dried over magnesium sulfate, filtered and evaporated in vacuo to yield a yellow oil (49.4 g, 92%). LCMS purity 100%, m/z 470 [M++Na]+.

Workup

  1. extractionextracted with EtOAc (3×600 ml)
  2. washThe combined organic extracts were washed with water (3×600 ml), brine (600 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b0a54dd38a314b189200280e9cf75d18
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

Loading…