Sulfuric Acid → HCID 11129651, compound

HRID 1463029Notes

Reaction equation

HRID 1463029 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18](=[CH2:20])[CH3:19].S(=O)(=O)(O)O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([O:16][C:18]([CH3:20])([CH3:19])[CH3:17])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 736104N-carbobenzyloxyalanine

Product 1

HCID 11129651HCID 11129651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of benzyloxycarbonyl-L-alanine (160 g., 0.72 mole), anhydrous dichloromethane (270 ml.), condensed isobutylene (700 ml.), and concentrated sulfuric acid (7.5 ml.) is shaken in a Parr apparatus at room temperature for 3 days. The isobutylene is allowed to evaporate at room temperature overnight and the residue is dissolved in 1 1. of ether. The resulting solution is washed with 1N sodium bicarbonate and brine. After drying over anhydrous MgSO4, the solvent is removed at reduced pressure to give 195 g. of benzyloxy-L-alanine, t-butyl ester as a yellow oil which is used without further purification.

Workup

  1. customto evaporate at room temperature overnight
  2. dissolutionthe residue is dissolved in 1 1
  3. washThe resulting solution is washed with 1N sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous MgSO4
  5. customthe solvent is removed at reduced pressure
  6. customto give 195 g
  7. customof benzyloxy-L-alanine, t-butyl ester as a yellow oil which is used without further purification

Sources & evidence

ORD record
ord-ae6cdcd80f04409990c7af0c21f22dea
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

Loading…