Hydrochloric Acid → (S)-1-[2-Methyl-3-[(4-nitrobenzofurazan-7-yl)thio]-1-oxopropyl]-L-proline

HRID 2417641Notes

Reaction equation

HRID 2417641 reaction equation
[SH:1][CH2:2][CH:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].Cl.C(=O)(O)[O-].[Na+].Cl[C:22]1[C:27]2=[N:28][O:29][N:30]=[C:26]2[C:25]([N+:31]([O-:33])=[O:32])=[CH:24][CH:23]=1>C(C(C)=O)C.O>[CH3:14][CH:3]([CH2:2][S:1][C:22]1[C:27]2[C:26](=[N:30][O:29][N:28]=2)[C:25]([N+:31]([O-:33])=[O:32])=[CH:24][CH:23]=1)[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25043NBD-ClHCID 516892Sodium BicarbonateHCID 128775471-(2-Methyl-3-sulfanylpropanoyl)-L-proline

Product 1

HCID 22823694(S)-1-[2-Methyl-3-[(4-nitrobenzofurazan-7-yl)thio]-1-oxopropyl]-L-proline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

3 Mg of 1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline was placed in a vial and dilute hydrochloric acid (0.1N, 2 ml) added to dissolve same. 3 Ml of 0.1M sodium bicarbonate solution was next added and the mixture was mixed in a vortex mixer. Thereafter, 3 ml of 1% (w/v) 4-chloro-7-nitrobenzofurazan in methyl ethyl ketone was added to the mixture, the vial was then closed and mixing was continued. The vial was held under running hot tap water, while shaking the vial, for about 2 minutes. The vial was then allowed to stand for 3 minutes, the organic (upper) layer was removed and was found to contain the title compound. The title compound was found to be fluorescent.

Workup

  1. additionadded
  2. dissolutionto dissolve same
  3. additionthe mixture was mixed in a vortex mixer
  4. customthe vial was then closed
  5. additionmixing
  6. waitto stand for 3 minutes
  7. customthe organic (upper) layer was removed

Sources & evidence

ORD record
ord-aeecc043a4414f69aa09b8dd580f5e66
Source dataset
uspto-grants-1984_09
Patent number
US04469870

Reaction notes

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