Hydrochloric Acid → HCID 178471595, compound

HRID 1489183Notes

Reaction equation

HRID 1489183 reaction equation
[H-].[Na+].[C:3]([N:5]=[C:6](SC)[NH:7][C@H:8]1[C@@:13]([OH:15])([CH3:14])[C:12]([CH3:17])([CH3:16])[O:11][C:10]2[CH:18]=[CH:19][C:20]([C:22]3[N:26]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:25]=[N:24][N:23]=3)=[CH:21][C:9]1=2)#[N:4].Cl.[CH2:38]([OH:40])[CH3:39]>>[C:3]([N:5]=[C:6]([O:40][CH2:38][CH3:39])[NH:7][C@H:8]1[C@@:13]([OH:15])([CH3:14])[C:12]([CH3:17])([CH3:16])[O:11][C:10]2[CH:18]=[CH:19][C:20]([C:22]3[N:26]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:25]=[N:24][N:23]=3)=[CH:21][C:9]1=2)#[N:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 178471596HCID 178471596, compound

Product 1

HCID 178471595HCID 178471595, compound

Procedure

Sodium hydride (0.03 g of an 80% dispersion in mineral oil) was added to ethanol (4 ml). After 5 minutes (3S,4R)-4-(3-cyano-2-methylisothioureido)-3,4-dihydro-6-(1-[3-ethoxycarbonylprop-1-yl]-1H-tetrazol-5-yl)-3-hydroxy-2,2,3-trimethyl-2H-benzo[b]pyran (see Example 75) (0.2 g) was added and the mixture was allowed to stand at room temperature for 16 hours. The solution was acidified to pH 3 with 2N hydrochloric acid and then was concentrated in vacuo. The residue was purified by chromatography on silica eluting with dichloromethane containing methanol (2.5%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was triturated with hexane to give the title compound as a foam, 0.09 g. Found: C,57.00; H,6.46; N,19.48; C23H31N7O5.0.1 hexane requires: C,57.35; H,6.60; N,19.83%.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by chromatography on silica eluting with dichloromethane
  3. additioncontaining methanol (2.5%)
  4. concentrationconcentrated in vacuo
  5. customto give an oil which
  6. customwas triturated with hexane

Sources & evidence

ORD record
ord-993a98df52414690b2d5867991a250ed
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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