1-[3-[[(Methylamino)thiocarbonyl]thio]propanoyl]-L-proline tertbutyl ester → HCID 13208309, compound

HRID 2419431Notes

Reaction equation

HRID 2419431 reaction equation
C([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:20])[CH2:13][CH2:14][S:15][C:16]([NH:18][CH3:19])=[S:17])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH3:19][NH:18][C:16]([S:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:21])=[O:5])=[O:20])=[S:17]

Participants

4

Reactant 1

HCID 132083071-[3-[[(Methylamino)thiocarbonyl]thio]propanoyl]-L-proline tertbutyl ester

Product 1

HCID 13208309HCID 13208309, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

1-[3-[[(Methylamino)thiocarbonyl]thio]propanoyl]-L-proline tertbutyl ester (0.98 g) is dissolved in a mixture of anisole (3.6 ml) and trifluoroacetic acid (7.5 ml). After one hour at room temperature the mixture is concentrated to dryness in vacuo and the residue precipitated from ether-hexane three times. This material is chromatographed on a column of silica gel with a solvent mixture of benzene-acetic acid (75:25) to yield 1-[3-[[(methylamino)thiocarbonyl]thio]propanoyl]-L-proline, Rf = 0.4 [silica gel-benzene:acetic acid (75:25)]. The dicyclohexylammonium salt has m.p. 127°-129°.

Workup

  1. concentrationAfter one hour at room temperature the mixture is concentrated to dryness in vacuo
  2. customthe residue precipitated from ether-hexane three times
  3. customThis material is chromatographed on a column of silica gel with a solvent mixture of benzene-acetic acid (75:25)

Sources & evidence

ORD record
ord-7fe93429d86949c4bf3a48e6a2ed8ca9
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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