Ethylamine → HCID 54018426, compound

HRID 1165120Notes

Reaction equation

HRID 1165120 reaction equation
Cl.C(O[C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][CH:10]=1)[NH2:7])C.[CH2:20]([NH2:22])[CH3:21]>>[CH2:20]([NH:22][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][CH:10]=1)[NH2:7])[CH3:21]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 24802217Ethyl 5-hydroxy-L-tryptophanate--hydrogen chloride (1/1)

Product 1

HCID 54018426HCID 54018426, compound

Conditions

Temperature
60 °C

Procedure

5-Hydroxytryptophan ethyl ester hydrochloride (69 mg, obtained from Sigma Chemical Co.) was dissolved in 0.5 ml of a 70% aqueous solution of ethylamine (obtained from Aldrich Chemical Co., Inc.) and heated on a steam bath at 60° C. under argon for twelve hours. The solvent was evaporated under a stream of argon. The resulting oil was dissolved in methanol/ether and acidified with gaseous HCl. Insolubles were allowed to precipitate and the solvent decanted. The hydrochloride salt of the product (40 mg) was dried under high vacuum. Mass spectroscopy (CI-NH3) showed a parent ion at 247 mass units (m+1).

Workup

  1. customThe solvent was evaporated under a stream of argon
  2. dissolutionThe resulting oil was dissolved in methanol/ether
  3. customto precipitate
  4. customthe solvent decanted
  5. dry with materialThe hydrochloride salt of the product (40 mg) was dried under high vacuum

Sources & evidence

ORD record
ord-a454d01311da494c894ca9a27e416295
Source dataset
uspto-grants-1990_03
Patent number
US04908322

Reaction notes

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