Hydrochloric Acid → HCID 22808898, compound

HRID 426961Notes

Reaction equation

HRID 426961 reaction equation
CCCCOC([NH:8][C:9]([C@@H:11]([NH:19][C:20]([C@@H:22]([NH:27][C:28]([C@@H:30]([NH:35][C:36]([C@@H:38]([NH2:49])[CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:42][CH:41]=1)=[O:37])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:29])[CH2:23][C:24]([OH:26])=[O:25])=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=O.Cl>O1CCOCC1.CCOCC>[NH2:49][C@H:38]([C:36]([NH:35][C@H:30]([C:28]([NH:27][C@H:22]([C:20]([NH:19][C@H:11]([C:9]([NH2:8])=[O:10])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:21])[CH2:23][C:24](=[O:25])[OH:26])=[O:29])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:37])[CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:42][CH:41]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 152221Butyloxycarbonyl-tryptophyl-leucyl-aspartyl-phenylalaninamide

Product 1

HCID 22808898HCID 22808898, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

7.1 g (10.5 mmoles) of BOC--Trp--Leu--Asp--Phe--NH2, prepared as described in Example 5, Step 2, are poured into 60 ml of hydrochloric acid in dioxane. The reaction mixture is initially turbid, but it gets clear within 3 minutes. After 10 minutes the solution is diluted with dry ether, the separated oily substance is solidified and filtered off. The resulting 6.96 g of hydrochloride are dissolved in 150 ml of warm water. Te pH of the solution is adjusted to 7 with solid sodium bicarbonate under cooling. The resulting suspension is filtered, and the precipitate is washed with a great proportion of water. 5.05 g (83.1 %) of H--Trp--Leu--Asp--Phe--NH2 are obtained; the chromatographically uniform substance melts at 228°-230° C. (decomposition). The product is identical with that obtained in Example 4, Step 4.

Workup

  1. filtrationfiltered off
  2. dissolutionThe resulting 6.96 g of hydrochloride are dissolved in 150 ml of warm water
  3. temperatureunder cooling
  4. filtrationThe resulting suspension is filtered
  5. washthe precipitate is washed with a great proportion of water
  6. custom5.05 g (83.1 %) of H--Trp--Leu--Asp--Phe--NH2 are obtained
  7. customthat obtained in Example 4, Step 4

Sources & evidence

ORD record
ord-e152b38241ee4299b6d3a77b4c0b8fc8
Source dataset
uspto-grants-1979_10
Patent number
US04172130

Reaction notes

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