Ammonia → HCID 9857516, compound

HRID 351924Notes

Reaction equation

HRID 351924 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1([C:20]2([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:15]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][N:12]3S(C)(=O)=O)=[CH:8][C:7]=2[CH2:6]1)[CH3:3].N.[Na]>O1CCCC1>[CH3:3][N:2]([CH2:4][C:5]1([C:20]2([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:15]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][NH:12]3)=[CH:8][C:7]=2[CH2:6]1)[CH3:1]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 22714699HCID 22714699, compound

Product 1

HCID 9857516HCID 9857516, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

3.75 g of the product obtained in Step 4 in 100 ml of tetrahydrofuran are added dropwise to 400 ml of liquid ammonia cooled to −50° C. 0.56 g of sodium are added in portions, and stirring is carried out for 15 minutes. The reaction is terminated by the addition of 2.65 g of ammonium chloride. The whole is allowed to return to ambient temperature to evaporate the ammonia, and is then taken up in water and extracted with ether. Drying, evaporation and recrystallisation from acetonitrile are carried out to yield the expected product.

Workup

  1. customThe reaction is terminated by the addition of 2.65 g of ammonium chloride
  2. customto return to ambient temperature
  3. customto evaporate the ammonia
  4. extractionextracted with ether
  5. customDrying
  6. customevaporation and recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-db396d705b3c44b6af789a7db553e64b
Source dataset
uspto-grants-2004_06
Patent number
US06743818B2

Reaction notes

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