Ammonia → HCID 86749072, compound

HRID 2211019Notes

Reaction equation

HRID 2211019 reaction equation
C([N:8]1[C@H:12]([C:13]([S:16]CC2C=CC(OC)=CC=2)([CH3:15])[CH3:14])[CH2:11][C@H:10]([CH2:26][S:27]CC2C=CC(OC)=CC=2)[C:9]1=[O:37])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>C1COCC1>[SH:16][C:13]([C@H:12]1[NH:8][C:9](=[O:37])[C@@H:10]([CH2:26][SH:27])[CH2:11]1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 86749071HCID 86749071, compound

Product 1

HCID 86749072HCID 86749072, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis-N-benzyl-4-[1-(4-methoxybenzylthio)-1-methylethyl]-2-(4-methoxybenzylthiomethyl)-4-butanelactam (compound No.14-1, 0.40 g) in THF (8 ml) was added in liquid ammonia (60 ml). To the solution sodium metal (0.12 g) was added in a small portion under nitrogen atmosphere. After an addition of ammonium chloride, ammonia was evaporated and a product was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The separated crystals were filtered to give 70 mg (46%) of the titled compound.

Workup

  1. customwas evaporated
  2. extractiona product was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. filtrationThe separated crystals were filtered

Sources & evidence

ORD record
ord-002f1446f02c4f7589657817e9d708c8
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

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