Hydrochloric Acid → HCID 14555499, compound

HRID 232053Notes

Reaction equation

HRID 232053 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:38])=[C:11]([N:14]4[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:37])[CH:21]([NH:29]C(OC(C)(C)C)=O)[CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:15]4)[N:12]=3)[C:7](=[O:39])[C:6]([C:40]([OH:42])=[O:41])=[CH:5]2)[CH2:3][CH2:2]1.Cl>C(O)C>[NH2:29][CH:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:11]2[N:12]=[C:13]3[C:8]([C:7](=[O:39])[C:6]([C:40]([OH:42])=[O:41])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:38])[CH2:15]1)=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14555496HCID 14555496, compound

Product 1

HCID 14555499HCID 14555499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.5 g (25 mmol) of [R-(R*,S*)]-1-cyclopropyl-7-[3-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid, 100 ml of 1.0M hydrochloric acid and 100 ml of ethanol was heated at reflux for three hours. The solution was filtered through a fiber glass pad to clarify and the solvent removed in vacuo. The residue was triturated with 100 ml of ethanol/ether (1:1) and the solid was removed by filtration. After washing with ethanol/ether (2×50 ml-1:1) and ether, the solid was dried in vacuo to give 10.2 g of the title compound, mp 216°-219°.

Workup

  1. temperatureat reflux for three hours
  2. filtrationThe solution was filtered through a fiber glass pad
  3. customthe solvent removed in vacuo
  4. customThe residue was triturated with 100 ml of ethanol/ether (1:1)
  5. customthe solid was removed by filtration
  6. washAfter washing with ethanol/ether (2×50 ml-1:1) and ether
  7. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-e0155e891fac4470afd9d445ce384a89
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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