Hydrogen Bromide → HCID 178419270, compound

HRID 1420134Notes

Reaction equation

HRID 1420134 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-9a738aa8b62b48abb50b45973cce94ef
Source dataset
uspto-grants-1999_03
Patent number
US05889056

Reaction notes

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