Ammonia → 1-[2-carbamoylmethyl-3-mercaptopropanoyl]-L-proline

HRID 1252833Notes

Reaction equation

HRID 1252833 reaction equation
[SH:1][CH2:2][CH:3]([CH2:14][C:15]([O:17]C)=O)[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].[NH3:19]>O>[C:15]([CH2:14][CH:3]([CH2:2][SH:1])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])(=[O:17])[NH2:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 539411441-[3-Mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-proline

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.1 g of the product from Example 62, Step (d) is dissolved in a mixture of water (40 ml) and concentrated ammonia (40 ml). After one hour the reaction mixture is concentrated in 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 in 1/3 volume
  2. washThe product is eluted with water
  3. extractionThe aqueous is extracted with ethyl acetate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9e0fa69636da40f8b8d84f2aea6a78ef
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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