Hydrochloric Acid → 1-{3-[(Triphenylmethyl)sulfanyl]propanoyl}-L-proline

HRID 894355Notes

Reaction equation

HRID 894355 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9]([S:28][CH2:29][CH2:30][C:31](Cl)=[O:32])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+].[OH-].[Na+].Cl>[OH-].[Na+]>[C:9]([S:28][CH2:29][CH2:30][C:31]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:32])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 145742L-ProlineHCID 21696466Disodium hydroxideHCID 860138253-(Tritylthio)propanoyl chloride

Product 1

HCID 537039881-{3-[(Triphenylmethyl)sulfanyl]propanoyl}-L-prolineYield 72%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.51 g (0.01 mole) of L-proline in 20 mls of 2 N NaOH is chilled in an icebath and treated with a total of 4.03 g (0.011 mol) of S-trityl-3-mercaptopropionyl chloride and 20 ml of 2 N NaOH NaOH in 5 equal and alternate portions with vigorous intermittent shaking and cooling in an ice bath. The solution is kept at an alkaline pH by the addition of more alkali when necessary. Upon completion of the addition of the reagents, the reaction mixture is stirred for an additional 15 min. at room temperature and then acidified to Congo red with cooling by dropwise treatment with concentrated HCl. The reaction is placed in a refrigerator overnight. The resultant precipitate is recovered by filtration, washed several times with ice water and dried in a dessicator over phosphorus pentoxide. Recrystallization in EtOH/H2O gave 3.2 g (72%) of the desired product. The NMR and IR showed the required peaks.

Workup

  1. temperaturecooling in an ice bath
  2. additionThe solution is kept at an alkaline pH by the addition of more alkali when necessary
  3. additionUpon completion of the addition of the reagents
  4. stirringthe reaction mixture is stirred for an additional 15 min. at room temperature
  5. customis placed in a refrigerator overnight
  6. filtrationThe resultant precipitate is recovered by filtration
  7. washwashed several times with ice water
  8. dry with materialdried in a dessicator over phosphorus pentoxide
  9. customRecrystallization in EtOH/H2O

Sources & evidence

ORD record
ord-185ca1a0b76f42f08417ea2637621287
Source dataset
uspto-grants-1981_08
Patent number
US04283328

Reaction notes

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