Carbonic acid-guanidine (1:1) → HCID 178508869, compound

HRID 2059722Notes

Reaction equation

HRID 2059722 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].O=[C:10]1[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12][CH:11]1[C:20](OC)=[O:21]>CN(C)C=O>[NH2:7][C:6]1[N:8]=[C:20]([OH:21])[C:11]2[CH2:12][CH2:13][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]3[C:10]=2[N:5]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 68799034Methyl 1-oxodecahydronaphthalene-2-carboxylate2×

Product 1

HCID 178508869HCID 178508869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
160 °C

Procedure

In a 500 mL round bottomed flask, a suspension of guanidine carbonate (11.1 g, 61.4 mmol) in N,N-dimethylformamide (100 mL) was heated with stirring to 160° C. for 10 minutes, and a solution of the product from Example 12A (6.46 g, 30.7 mmol) in N,N-dimethylformamide (15 mL) was added dropwise over 2 minutes. The flask that contained the product from Example 12A was rinsed with an additional 10 mL of N,N-dimethylformamide and this was added to the reaction over 2 minutes. The reaction was heated to 165° C. for 20 minutes, cooled to room temperature and partitioned between 1 M sodium hydroxide (650 mL) and ether (200 mL). The layers were separated and the ether layer was extracted with 1 M sodium hydroxide (25 mL). The ether layer was disposed of. The combined aqueous sodium hydroxide layers were cooled in an ice bath and acidified to pH ˜7 with concentrated hydrochloric acid. After standing at ambient temperature for 15 minutes, the resulting solid was collected by filtration, washed with water and dried overnight in a drying oven with heating under vacuum to provide the title compound: 1H NMR (DMSO-d6) δ 0.78-0.96 (m, 1H), 1.00-1.35 (m, 5H), 1.61-1.74 (m, 3H), 1.75-192 (m, 2H), 2.01-2.18 (m, 1H), 2.28-2.58 (m, 2H), 6.13 (br s, 2H), 10.66 (s, 1H); MS (DCl/NH3) m/z 220 (M+H)+.

Workup

  1. temperaturewas heated
  2. washwas rinsed with an additional 10 mL of N,N-dimethylformamide
  3. additionthis was added to the reaction over 2 minutes
  4. temperatureThe reaction was heated to 165° C. for 20 minutes
  5. temperaturecooled to room temperature
  6. custompartitioned between 1 M sodium hydroxide (650 mL) and ether (200 mL)
  7. customThe layers were separated
  8. extractionthe ether layer was extracted with 1 M sodium hydroxide (25 mL)
  9. temperatureThe combined aqueous sodium hydroxide layers were cooled in an ice bath
  10. waitAfter standing at ambient temperature for 15 minutes
  11. filtrationthe resulting solid was collected by filtration
  12. washwashed with water
  13. customdried overnight in a drying oven
  14. temperaturewith heating under vacuum

Sources & evidence

ORD record
ord-4ebe5a2b256c43459912891683c564ea
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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