Thiazolidine → HCID 53784898, compound

HRID 892609Notes

Reaction equation

HRID 892609 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=O)=[O:9].C1C=CC2N(O)N=NC=2C=1.[S:28]1[CH2:32][CH2:31][NH:30][CH2:29]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([N:30]1[CH2:31][CH2:32][S:28][CH2:29]1)=[O:14])=[O:9]

Participants

7

Reactant 4

HCID 10444ThiazolidineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 28789692HCID 28789692, compound

Product 1

HCID 53784898HCID 53784898, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-25 °C

Procedure

N-[(2-Oxo-1-pyrrolidinyl)acetyl]-L-proline as prepared in Example 1-B) (623 mg) was suspended in a mixture of methylene chloride (3 ml) and DMF (5 ml), to which were added HOBt (530 mg) and thiazolidine (0.21 ml). The mixture was cooled to -25° C. and DCC (588 mg) was added thereto. The mixture was stirred at a temperature of -25°-0° C. for 3 hours and at room temperature for 12 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 468 mg of 3-{N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-prolyl}thiazolidine.

Workup

  1. filtrationThe precipitated dicyclohexylurea was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6be11c1451834a5381b894b980be3703
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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