Hydrogen Bromide → HCID 178419269, compound

HRID 427182Notes

Reaction equation

HRID 427182 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-04c226e4c8a34e72ad24d61b137d785c
Source dataset
uspto-grants-2001_11
Patent number
USRE037438E1

Reaction notes

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