Sodium Carbonate → HCID 59656134, compound

HRID 2054555Notes

Reaction equation

HRID 2054555 reaction equation
[C:1]12([C:11]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]O)[C:14]([SH:21])=[N:13][N:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O-])([O-])=O.[Na+].[Na+]>Cl>[C:1]12([C:11]3[N:15]4[C:14]([S:21][CH2:19][CH2:18][CH2:17][CH2:16]4)=[N:13][N:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 178520655HCID 178520655, compound

Product 1

HCID 59656134HCID 59656134, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-[3-(1-adamantyl)-5-mercapto-4H-1,2,4-triazol-4-yl]butan-1-ol (3-36) (60 mg) in conc. HCl (6 mL) was heated at 65° C. for 20 h. The cooled solution was added dropwise to 10% aqueous Na2CO3 (75 mL). The gum that precipitated was extracted four times with CH2Cl2. The combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by reverse phase HPLC on a C-18 silica gel column using an acetonitrile-0.1% trifluoroacetic acid gradient. Fractions containing the product were combined and rendered basic with excess 10% sodium carbonate. After removing most of the acetonitrile in vacuo, the basic solution was extracted five times with CH2Cl2. The combined extracts were dried (MgSO4) and evaporated in vacuo to give 3-(1-adamantyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3]thiazepine (3-37).

Workup

  1. customThe gum that precipitated
  2. extractionwas extracted four times with CH2Cl2
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by reverse phase HPLC on a C-18 silica gel column
  6. additionFractions containing the product
  7. customAfter removing most of the acetonitrile in vacuo
  8. extractionthe basic solution was extracted five times with CH2Cl2
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-fc582721ae28449994ba5a8e4f21fc78
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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