Hydrogen Bromide → HCID 178419269, compound

HRID 361734Notes

Reaction equation

HRID 361734 reaction equation
[BrH:1].C(OC([NH:9][CH2:10][C:11]#[C:12][CH2:13][NH:14][C:15](=[NH:18])[CH2:16][F:17])=O)CCC.Br>C(O)(=O)C>[BrH:1].[BrH:1].[NH2:9][CH2:10][C:11]#[C:12][CH2:13][NH:14][C:15](=[NH:18])[CH2:16][F:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178419546HCID 178419546, compound

Product 1

HCID 178419269HCID 178419269, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-Butoxycarbonylamino-4-(1-imino-2-fluoroethylamino)but-2-yne hydrobromide (500 mg) was deprotected by dissolving in glacial acetic acid (10 ml), cooling until the solution almost solidified and adding HBr in acetic acid (45% wv, 1.8 ml). The mixture was stirred with cooling for 1 h then at room temperature for 1 h. After this time the mother liquor was decanted off and the sticky residue subjected to an oil pump vacuum to remove residual solvent. The resulting material was triturated with dry diethyl ether (×2), filtered off and washed with more dry diethyl ether. The yellow solid was recrystallised from ethanol/diethyl ether and finally dried in a drying pistol to yield 1-amino-4-(1-imino-2-fluoroethylamino)but-2-yne dihydrobromide, Mpt 174°-176.5° C.(dec.), FAB M.S. M+1+ 144.

Workup

  1. temperaturecooling until the solution
  2. temperaturewith cooling for 1 h
  3. customAfter this time the mother liquor was decanted off
  4. customto remove residual solvent
  5. customThe resulting material was triturated with dry diethyl ether (×2)
  6. filtrationfiltered off
  7. washwashed with more dry diethyl ether
  8. customThe yellow solid was recrystallised from ethanol/diethyl ether
  9. customfinally dried in a drying pistol

Sources & evidence

ORD record
ord-2401c672f1bd4abab1164be720eb6333
Source dataset
uspto-grants-1999_02
Patent number
US05866612

Reaction notes

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