Ammonia → HCID 53950354, compound

HRID 1583567Notes

Reaction equation

HRID 1583567 reaction equation
C([S:8][CH2:9][C:10]1([CH3:21])[CH2:14][CH2:13][N:12]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:11]1=[O:20])C1C=CC=CC=1.O1CCCC1.N.[Na]>CO>[SH:8][CH2:9][C:10]1([CH3:21])[CH2:14][CH2:13][N:12]([C@@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:11]1=[O:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 54318378HCID 54318378, compound

Product 1

HCID 53950354HCID 53950354, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Two grams of (αS)-3-(benzylmercaptomethyl)α,3-dimethyl-2-oxo-1-pyrrolidineacetic acid were dissolved in about 15 ml. of tetrahydrofuran. This solution was then added to liquid ammonia. Small pieces of sodium metal were added until a blue color persisted. The reaction was then quenched by the addition of about two grams of ammonium chloride. The ammonia was evaporated and water was added to the residue. The slurry was made acidic with hydrochloric acid, saturated with sodium chloride and the acidic solution was extracted with chloroform. The chloroform extract was washed with a saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness. Two crystallizations of the resulting solid from diethylether/Skelly B gave 0.5 g. of the desired title product, m.p. about 132°-133° C. [α]D25 =-23.78° (c=1, methanol).

Workup

  1. customThe reaction was then quenched by the addition of about two grams of ammonium chloride
  2. customThe ammonia was evaporated
  3. additionwater was added to the residue
  4. extractionthe acidic solution was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with a saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness
  9. customTwo crystallizations of the resulting solid from diethylether/Skelly B
  10. customgave 0.5 g

Sources & evidence

ORD record
ord-e1905b11eb0e4fdaa6fc9d091a2210ba
Source dataset
uspto-grants-1985_11
Patent number
US04552889

Reaction notes

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