HCID 13017212, compound → HCID 131711508, compound

HRID 262703Notes

Reaction equation

HRID 262703 reaction equation
O.[SH:2][CH2:3][CH2:4][C:5]([NH:7][N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:6].S[CH2:17][CH2:18][C:19](NN1CCC[C@H]1C(O)=O)=O.C(N=NNC1C=CC(C)=CC=1)CC>CCOCC>[SH:2][CH2:3][CH2:4][C:5]([NH:7][N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([O:12][CH2:17][CH2:18][CH3:19])=[O:11])=[O:6]

Participants

4

Reactant 2

HCID 13017212HCID 13017212, compoundHCID 88629803HCID 88629803, compound

Product 1

HCID 131711508HCID 131711508, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 6.81 g. of 1-[(3-mercapto-1-oxopropyl)amino]-L-proline, hemihydrate in 50 ml. of ether, there is added dropwise a solution of 8.75 g. of 1-propyl-3-p-tolyltriazene in 100 ml. of ether and the mixture is heated to reflux for 4 hours. The reaction mixture is then cooled, filtered and extracted twice with 50 ml. portions of 5% hydrochloric acid and then with 50 ml. portions of 5% sodium bicarbonate solution. The ether solution is then washed with 100 ml. of saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude product.

Workup

  1. additionTo a stirred suspension of 6.81 g
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationfiltered
  5. extractionextracted twice with 50 ml
  6. washThe ether solution is then washed with 100 ml
  7. dry with materialof saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d763dafe12e64cc7951ac005c87e2953
Source dataset
uspto-grants-1979_05
Patent number
US04154934

Reaction notes

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