Ammonia → HCID 13208321, compound

HRID 1252836Notes

Reaction equation

HRID 1252836 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:19])[CH2:13][CH2:14][S:15]C(=O)C)([CH3:4])([CH3:3])[CH3:2].N>>[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:19])[CH2:13][CH2:14][SH:15])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 132082993-acetylthiopropanoyl-L-proline-t-butyl ester2×

Product 1

HCID 13208321HCID 13208321, compound

Procedure

The product from step b, 3-acetylthiopropanoyl-L-proline-t-butyl ester, 0.5 g, was mixed with 4.5 ml of 5.5N methanolic ammonia at room temperature under nitrogen for one hour. The solvent was then removed at 25° C. with a rotary evaporator. After the product was taken up in methanol and reevaporated twice more in the rotary evaporator, the clear oily residue was dissolved in ethyl ether, washed twice with 5% potassium bisulphate and once with saturated NaCl, dried over MgSO4 and filtered. Residual solvent was removed in vacuo to yield a clear oily product, migrating as a single spot on thin layer chromatography in three separate solvent systems.

Workup

  1. customThe solvent was then removed at 25° C. with a rotary evaporator
  2. customreevaporated twice more in the rotary evaporator
  3. dissolutionthe clear oily residue was dissolved in ethyl ether
  4. washwashed twice with 5% potassium bisulphate and once with saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customResidual solvent was removed in vacuo
  8. customto yield a clear oily product
  9. customseparate solvent systems

Sources & evidence

ORD record
ord-7cf546b2d70f4a379ff33dadd60d2d39
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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