Carbon Dioxide → HCID 11129651, compound

HRID 1755821Notes

Reaction equation

HRID 1755821 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].C(=O)=O>C(Cl)Cl.S(=O)(=O)(O)O>[C:18]([O:15][C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:20])([CH3:19])[CH3:17]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 8255Isobutylene2×HCID 736104N-carbobenzyloxyalanine

Product 1

HCID 11129651HCID 11129651, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Benzyloxycarbonyl-L-alanine (15.0 g) (67.2 mmol) was dissolved in methylene chloride with about 1 mL of concentrated sulfuric acid. Isobutylene was added via a dry-ice, cold finger trap. The solution was allowed to warm to room temperature and left stirring overnight. The solution was charged with isobutylene again and left stirring overnight. The solution was extracted with 0.8N aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and evaporated under vacuum to give benzyloxycarbonyl-L-alanine t-butyl ester. 1H NMR (CDCl3) δ7.35 (s, 5H), 5.12 (s, 2H), 4.23 (m, 2H), 1.45-1.30 (s/d, 12H).

Workup

  1. waitleft
  2. waitleft
  3. stirringstirring overnight
  4. extractionThe solution was extracted with 0.8N aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-c6a367fda1e448a7abe9f0ad3e64c08c
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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