Benzene → HCID 54379955, compound

HRID 1795720Notes

Reaction equation

HRID 1795720 reaction equation
[NH:1]([C:11]([O:13]C(C)(C)C)=O)[C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5](=[O:7])[OH:6].C1C=CC=CC=1.C=[O:25].[C:26]1([CH3:36])[CH:31]=CC(S(O)(=O)=O)=C[CH:27]=1.CC[O:39][CH2:40]C>CC#N.O>[C:26]([O:25][C:40]([C@H:11]1[NH:1][CH:2]([CH2:3][CH2:4][C:5]([OH:6])=[O:7])[C:8](=[O:10])[O:13]1)=[O:39])([CH3:36])([CH3:31])[CH3:27]

Participants

8

Reactant 5

HCID 241BenzeneHCID 712FormaldehydeHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 2724758Boc-Glu-OH

Product 1

HCID 54379955HCID 54379955, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1077 g (4.36 mols) of Boc-L-Glu, 2, was dissolved in 1 L of CH3CN with warming. This was poured into a 5 L three neck flask. To this solution 3 L of benzene, 196 g (6.54 mols) of paraformaldehyde, and 40 g (0.26 mols) of p-toluene sulfonic acid were added. Equipping the round bottom flasks with two Dean-Stark apparati, dual condensers at −10° C., and a mechanical stirrer, the reaction mixture was brought to 70° C. and refluxed for 6 hours (100 ml of water was collected from the Dean-Stark apparati indicating complete reaction). The reaction mixtures, clear reddish-brown solutions, were allowed to cool to room temperature, and were rotoevaporated to a reddish-brown oil. The oil was redissolved in 2 L of ether and was extracted three times with 1 L each of water. The aqueous layers were combined and were extracted with 2 L of ether to remove the product which was in the water. Both ether layers were combined, dried over Na2SO4, filtered, and roto-evaporated to a clear yellow oil. This was dried in vacuo to obtain 952 g (3.67 mols), 84.3% yield of impure 3.

Workup

  1. temperaturewith warming
  2. customat −10° C.
  3. customa mechanical stirrer, the reaction mixture was brought to 70° C.
  4. customwas collected from the Dean-Stark apparati
  5. customreaction)
  6. customThe reaction mixtures, clear reddish-brown solutions
  7. extractionwas extracted three times with 1 L each of water
  8. extractionwere extracted with 2 L of ether
  9. customto remove the product which
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customroto-evaporated to a clear yellow oil
  13. customThis was dried in vacuo
  14. customto obtain 952 g (3.67 mols), 84.3% yield of impure 3

Sources & evidence

ORD record
ord-d284c463b5fc410fa8b2ec0c59f0f4b4
Source dataset
uspto-grants-2006_04
Patent number
US07029695B2

Reaction notes

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