Triethylamine → HCID 20564727, compound

HRID 848844Notes

Reaction equation

HRID 848844 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:8][CH:7]=[CH:6][CH2:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12].C(N(CC)CC)C.N([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N+]=[N-]>C1COCC1>[C:27]([O:26][C:24]([NH:1][CH2:2][C:3]1[CH2:8][CH:7]=[CH:6][CH2:5][C:4]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 20564771HCID 20564771, compound

Product 1

HCID 20564727HCID 20564727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of β-(2-aminomethyl-1,4-cyclohexadienyl)propionic acid (1.40 L g., 7.7 mmoles) and triethylamine (2.02 g., 20 mmoles) in 50% aqueous THF (20 ml.) was added a solution of t-butyl azidoformate (1.43 g., 10 mmoles) in THF (5 ml.) and the reaction mixture was stirred overnight at room temperature. The mixture was washed with ether (2×20 ml) and the aqueous layer was acidified to pH 2 with dil. hydrochloric acid. The mixture was extracted with chloroform (4×30 ml.) and the combined extracts were washed with water and dried. Evaporation of the extracts under reduced pressure afforded β-(2-tert.-butoxycarbonylaminomethyl-1,4-cyclohexadienyl)propionic acid as a colorless oil. Yield, 2.10 g. (97%).

Workup

  1. washThe mixture was washed with ether (2×20 ml)
  2. extractionThe mixture was extracted with chloroform (4×30 ml.)
  3. washthe combined extracts were washed with water
  4. customdried
  5. customEvaporation of the extracts under reduced pressure

Sources & evidence

ORD record
ord-424610a688a043c1a85682f37bc1671f
Source dataset
uspto-grants-1981_10
Patent number
US04297489

Reaction notes

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