Hydrochloric Acid → HCID 69889711, compound

HRID 2088124Notes

Reaction equation

HRID 2088124 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@:14]([F:27])([C:16]3[N:20]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10]([O:28][Si](C(C)(C)C)(C)C)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCOCC.CO>[CH2:1]([N:8]1[C@@H:13]2[C@:14]([F:27])([C:16]3[N:20]([CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10]([OH:28])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69890742HCID 69890742, compound

Product 1

HCID 69889711HCID 69889711, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-(tert-butyldimethylsilyloxy)-6-fluoro-6-[1-(2-methoxyethoxymethyl)-1H-tetrazol-5-yl]-1-phenyl-8-azabicyclo[3.2.1]octane (Description 44a; 4.5 g, 7.7 mmol), 1 M solution of hydrogen chloride in ether (30 ml) and methanol (50 ml) was stirred at room temperature for 90 minutes. The reaction mixture was treated with saturated aqueous NaHCO, and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 20-80%) to give the title compound (2.5 g, 70%).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 20-80%)

Sources & evidence

ORD record
ord-8b7088f311a443118fdaeb33f8e5514f
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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