Ammonium bifluoride → HCID 118380314, compound

HRID 708343

Reaction equation

HRID 708343 reaction equation
C1CCN(CCOC(C2C=CC(Cl)=CC=2)C2C=CC=CC=2)CC1.Cl.[C:25]([O:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36](/[C:38](=[N:59]/[O:60][C:61]([CH3:70])([CH3:69])[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])/[C:39]([NH:41][C@@H:42]2[C:45](=[O:46])[NH:44][C@@H:43]2[CH2:47][NH:48][CH2:49][CH2:50][O:51][Si](C(C)(C)C)(C)C)=[O:40])[N:37]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].F.[F-].[NH4+]>CN(C=O)C.CN1C(=O)CCC1.O>[C:25]([O:29][C:30]([NH:32][C:33]1[S:34][CH:35]=[C:36](/[C:38](=[N:59]/[O:60][C:61]([CH3:70])([CH3:69])[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])/[C:39]([NH:41][C@@H:42]2[C:45](=[O:46])[NH:44][C@@H:43]2[CH2:47][NH:48][CH2:49][CH2:50][OH:51])=[O:40])[N:37]=1)=[O:31])([CH3:27])([CH3:28])[CH3:26]

Participants

6

Reactant 3

HCID 14935Ammonium bifluorideHCID 161104Cloperastine HydrochlorideHCID 140689321HCID 140689321, compound

Product 1

HCID 118380314HCID 118380314, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22708839HCID 22708839, compoundSolvent

Procedure

Prepared according to Seki et al. Synlett 1995, 609-611. To a solution of tert-butyl 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-(((2-((tert-butyldimethylsilyl)oxy)ethyl)amino)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoate (111 mg, 0.162 mmol) in DMF:NMP (2.7:1, 1.62 mL) was added ammonium fluoride hydrofluoride (37.0 mg, 0.648 mmol). After stirring for 65 h, the solution was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford crude title compound (92 mg, 99%). The crude material was used directly in step 3. LCMS: R=0.76 min, m/z 571.3 (M+1) Method 2m_acidic.

Workup

  1. customPrepared
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dc75cf636b5476cab09d566abb21a73
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Linked notes

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