Hydrochloric Acid → N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-(4-{1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenyl)hex-5-enamide

HRID 1612556Notes

Reaction equation

HRID 1612556 reaction equation
[CH3:1][N:2]([CH2:46][CH:47]([OH:56])[CH:48]([OH:55])[CH:49]([OH:54])[CH:50]([OH:53])[CH2:51][OH:52])[C:3](=[O:45])[CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:18]([CH2:19][CH2:20][CH:21]([O:29][Si](C(C)(C)C)(C)C)[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17](=[O:37])[N:16]2[C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[CH:11][CH:10]=1.Cl.[OH-].[Na+]>CO>[CH3:1][N:2]([CH2:46][CH:47]([OH:56])[CH:48]([OH:55])[CH:49]([OH:54])[CH:50]([OH:53])[CH2:51][OH:52])[C:3](=[O:45])[CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH:18]([CH2:19][CH2:20][CH:21]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[OH:29])[C:17](=[O:37])[N:16]2[C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68552127N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide

Product 1

HCID 68551149N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-(4-{1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenyl)hex-5-enamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

70 mg of N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide are dissolved in 6 ml of methanol. 0.1 N HCl(aq) is then added, and the mixture is stirred at room temperature overnight. The mixture is then neutralized with 1 N aqueous sodium hydroxide solution and concentrated using a rotary evaporator. The residue is stirred with dichloromethane and filtered and the mother liquor is concentrated using a rotary evaporator. The product is obtained following purification by preparative HPLC: C31H44F2N2O8 (682) MS (ESI): M+−18

Workup

  1. concentrationconcentrated
  2. customa rotary evaporator
  3. stirringThe residue is stirred with dichloromethane
  4. filtrationfiltered
  5. concentrationthe mother liquor is concentrated
  6. customa rotary evaporator
  7. customThe product is obtained
  8. custompurification by preparative HPLC

Sources & evidence

ORD record
ord-d9be8a5986d84ccca1deed4e96254e2e
Source dataset
uspto-grants-2006_01
Patent number
US06992067B2

Reaction notes

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