1,5-Naphthalenedisulfonic acid → HCID 131714450, compound

HRID 637667Notes

Reaction equation

HRID 637667 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:63])[CH2:21][N:19]2[CH2:20][CH:5]([CH2:6][C@:7]([C:59]([O:61][CH3:62])=[O:60])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:56][CH3:57])([C@@H:41]([O:52][C:53]([CH3:55])=[O:54])[C@@:42]8([O:48][C:46](=[O:47])[N:45]([CH2:49][CH2:50][Cl:51])[C:43]8=[O:44])[C@@H:31]5[N:30]([CH3:58])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1.[C:64]1([S:78]([OH:81])(=[O:80])=[O:79])[C:73]2[CH:72]=[CH:71][CH:70]=[C:69]([S:74]([OH:77])(=[O:76])=[O:75])[C:68]=2[CH:67]=[CH:66][CH:65]=1>CO>[CH3:1][CH2:2][C@@:3]1([OH:63])[CH2:21][N:19]2[CH2:20][CH:5]([CH2:6][C@:7]([C:59]([O:61][CH3:62])=[O:60])([C:22]3[CH:23]=[C:24]4[C@:32]56[C@@H:36]7[C@:37]([CH2:56][CH3:57])([C@@H:41]([O:52][C:53]([CH3:55])=[O:54])[C@@:42]8([O:48][C:46](=[O:47])[N:45]([CH2:49][CH2:50][Cl:51])[C:43]8=[O:44])[C@@H:31]5[N:30]([CH3:58])[C:25]4=[CH:26][C:27]=3[O:28][CH3:29])[CH:38]=[CH:39][CH2:40][N:35]7[CH2:34][CH2:33]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:9]=3[CH2:17][CH2:18]2)[CH2:4]1.[C:64]1([S:78]([O-:81])(=[O:80])=[O:79])[C:73]2[CH:72]=[CH:71][CH:70]=[C:69]([S:74]([O-:77])(=[O:76])=[O:75])[C:68]=2[CH:67]=[CH:66][CH:65]=1

Participants

4

Reactant 2

HCID 66661,5-Naphthalenedisulfonic acidHCID 49967methyl (13S,17S)-13-[(1'R,5S,9'R,11'R,12'R,19'R)-11'-acetyloxy-3-(2-chloroethyl)-12'-ethyl-5'-methoxy-8'-methyl-2,4-dioxospiro[1,3-oxazolidine-5,10'-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene]-4'-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

Product 1

HCID 131714450HCID 131714450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1% (w/v) solution of vinzolidine free base (95+% purity) in methanol is added dropwise with stirring a stoichiometric amount (1 mole per mole) of a 2% methanolic solution of 1,5-naphthalenedisulfonic acid. The resulting solution was allowed to stand at ambient temperature for about two hours, during which time period crystallization of the vinzolidine 1,5-naphthalenedisulfonate salt begins. The crystallizing solution is kept at about 0° C. overnight and is then filtered. The filter cake is washed with a small amount of methanol and then dried in vacuo overnight at ambient temperature. The salt is then allowed to stand in air for about two hours. The yield of vinzolidine 1,5-naphthalenedisulfonate is 95-97%.

Workup

  1. customto stand at ambient temperature for about two hours, during which time period crystallization of the vinzolidine 1,5-naphthalenedisulfonate salt
  2. filtrationis then filtered
  3. washThe filter cake is washed with a small amount of methanol
  4. customdried in vacuo overnight at ambient temperature
  5. waitto stand in air for about two hours

Sources & evidence

ORD record
ord-efe1a20ce64e4286a46355cc154f3425
Source dataset
uspto-grants-1985_12
Patent number
US04558053

Reaction notes

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