Hydrogen Bromide → HCID 178419270, compound

HRID 1271008Notes

Reaction equation

HRID 1271008 reaction equation
[BrH:1].C([C:6]([NH:21]C(OC(C)(C)C)=O)([CH2:10][S:11](=[O:20])(=[O:19])[CH2:12][CH2:13][NH:14][C:15](=[NH:18])[CH2:16][F:17])[C:7]([OH:9])=[O:8])(C)(C)C.Br>C(O)(=O)C>[BrH:1].[BrH:1].[NH2:21][CH:6]([CH2:10][S:11](=[O:20])(=[O:19])[CH2:12][CH2:13][NH:14][C:15](=[NH:18])[CH2:16][F:17])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178419548HCID 178419548, compound

Product 1

HCID 178419270HCID 178419270, compoundYield 173.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

t-Butyl-2-t-butoxycarbonylamino-6-(1-imino-2-fluoroethylamino)-4,4-dioxo-4-thiahexanoic acid hydrobromide (300 mg) was dissolved in glacial acetic acid (4.5 ml), and cooled whilst HBr in acetic acid (45% w/v, 1.5 ml) was added. The mixture was then stirred at room temperature for 2 h. The volatile materials were evaporated in vacuo and the residue dissolved in water. The solution was evaporated to dryness in vacuo, and this process repeated twice more. Ethanol was added to the residue and the mixture concentrated in vacuo to an off-white foam. The material could be further purified by dissolving in a minimum of warm ethanol and precipitating the product with ether to yield a white hygroscopic solid (220 mg) as the dihydrate.

Workup

  1. additionwas added
  2. customThe volatile materials were evaporated in vacuo
  3. dissolutionthe residue dissolved in water
  4. customThe solution was evaporated to dryness in vacuo
  5. additionEthanol was added to the residue
  6. concentrationthe mixture concentrated in vacuo to an off-white foam
  7. customThe material could be further purified
  8. dissolutionby dissolving in a minimum of warm ethanol
  9. customprecipitating the product with ether

Sources & evidence

ORD record
ord-3db66b38e3b74e54ad1fe61cd91e0bb4
Source dataset
uspto-grants-2007_04
Patent number
USRE039576E1

Reaction notes

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