Acetic Acid → 1-[2-carbamoylmethyl-3-mercaptopropanoyl]-L-proline

HRID 2309067Notes

Reaction equation

HRID 2309067 reaction equation
C([S:4][CH2:5][CH:6]([CH2:17][C:18]([O:20]C)=O)[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=O)C.CO.C(O)(=O)C.[NH3:28]>O>[C:18]([CH2:17][CH:6]([CH2:5][SH:4])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=[O:20])[NH2:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 887MethanolHCID 541123831-[3-(Acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-proline

Product 1

HCID 867357171-[2-carbamoylmethyl-3-mercaptopropanoyl]-L-proline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.1 g. of the product from Example 81 is dissolved in a mixture of water (40 ml.) and concentrated ammonia (40 ml.). After one hour the reaction mixture is concentrated to 1/3 volume, and applied to a column of Dowex 50 resin in the hydrogen cycle. The product is eluted with water. The aqueous is extracted with ethyl acetate and then concentrated to dryness to yield 1.4 g. of the named product Rf 0.50 (silica gel-Chloroform:methanol:acetic acid:water).

Workup

  1. concentrationAfter one hour the reaction mixture is concentrated to 1/3 volume
  2. washThe product is eluted with water
  3. extractionThe aqueous is extracted with ethyl acetate
  4. concentrationconcentrated to dryness
  5. customto yield 1.4 g

Sources & evidence

ORD record
ord-810d1ce38f6345e9bde0bce420989e9a
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

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