Hydrogen Bromide → 790704-50-6

HRID 1893866Notes

Reaction equation

HRID 1893866 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:62]=[CH:61][C:15]([O:16][CH2:17][C:18]3([O:42][P:43]([O:53]CC4C=CC=CC=4)([O:45]CC4C=CC=CC=4)=[O:44])[CH2:23][CH2:22][N:21]([C:24]4[CH:33]=[C:32]5[C:27]([C:28](=[O:40])[C:29]([C:37]([OH:39])=[O:38])=[CH:30][N:31]5[CH:34]5[CH2:36][CH2:35]5)=[CH:26][C:25]=4[F:41])[CH2:20][CH2:19]3)=[C:14]([F:63])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].Br.O>C(#N)C.C(O)(=O)C>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:62]=[CH:61][C:15]([O:16][CH2:17][C:18]3([O:42][P:43]([OH:53])([OH:45])=[O:44])[CH2:23][CH2:22][N:21]([C:24]4[CH:33]=[C:32]5[C:27]([C:28](=[O:40])[C:29]([C:37]([OH:39])=[O:38])=[CH:30][N:31]5[CH:34]5[CH2:35][CH2:36]5)=[CH:26][C:25]=4[F:41])[CH2:20][CH2:19]3)=[C:14]([F:63])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 58916248HCID 58916248, compound

Product 1

HCID 44201350790704-50-6

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

27 g 7-[4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-(bis-benzyloxy-phosphoryloxy)-piperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (MW: 886.85, 30.44 mmol) were suspended in 600 ml acetonitrile and treated with 53 ml of a 33% solution of anhydrous hydrobromic acid in acetic acid. The yellow suspension was diluted with 150 ml of acetic acid and was heated to 45° C. The reaction was monitored by HPLC/MS and was complete after 3 hours. The sticky suspension was added to 1.5 L of water under stirring. The off white crystals were collected, washed with 300 ml water, 150 ml ethanol and 150 ml ether. The solid was suspended in 1.3 L water and treated with 35 ml (35 mmol) of a 1M aqueous sodium hydroxide solution. The solid dissolved, and the brown-yellow solution was treated with 15 g of activated charcoal and filtered. The filtrate was extracted with 3 portions of 200 ml of a 95/5 dichloromethane/methanol mixture. The water layer was treated with 40 ml of 1 M HCl solution and the product crystallized by stirring. The solid was collected and dried. Yield: 17.3-g, 80.4%. MS: 609.7 (M+H)+, 607.8 (M+H)−, Method ESI+, ESI−.

Workup

  1. customThe off white crystals were collected
  2. washwashed with 300 ml water, 150 ml ethanol and 150 ml ether
  3. additiontreated with 35 ml (35 mmol) of a 1M aqueous sodium hydroxide solution
  4. dissolutionThe solid dissolved
  5. additionthe brown-yellow solution was treated with 15 g of activated charcoal
  6. filtrationfiltered
  7. extractionThe filtrate was extracted with 3 portions of 200 ml of a 95/5 dichloromethane/methanol mixture
  8. additionThe water layer was treated with 40 ml of 1 M HCl solution
  9. customthe product crystallized
  10. stirringby stirring
  11. customThe solid was collected
  12. customdried

Sources & evidence

ORD record
ord-e1fe639419db494da6a6a9ae305ee0cb
Source dataset
uspto-grants-2013_08
Patent number
US08513231B2

Reaction notes

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