1,1'-Carbonyldiimidazole → HCID 68646904, compound

HRID 1162731Notes

Reaction equation

HRID 1162731 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[CH2:29]([O:31][C:32](=[O:41])[C:33]([N:35]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36]1)=[O:34])[CH3:30]>C1COCC1.CCN(C(C)C)C(C)C>[CH2:29]([O:31][C:32](=[O:41])[C:33]([N:35]1[CH2:39][CH2:38][CH:37]([NH:40][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])[CH2:36]1)=[O:34])[CH3:30]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 68647069HCID 68647069, compound

Product 1

HCID 68646904HCID 68646904, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
25 °C

Procedure

106.3 5-Chloro-thiophene-2-carboxylic acid (0.94 g) was dissolved in THF (10 ml) and CDI (0.94 g) was added. This mixture was stirred at 25° C. for 30 min. A solution of (3-amino-pyrrolidin-1-yl)-oxo-acetic acid ethyl ester trifluoroacetate (1.57 g), dissolved in THF (10 ml) and DIEA (0.89 ml), is added to the reaction mixture. The obtained reaction mixture was stirred for 18 h at 25° C. Finally, the reaction mixture was evaporated to dryness. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2 to CH2Cl2/MeOH 98:2) to give {3-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidin-1-yl}-oxo-acetic acid ethyl ester (1.9 g) as an orange oil. MS 331.3 ([M+H]+, Cl-isotopes).

Workup

  1. customThe obtained reaction mixture
  2. stirringwas stirred for 18 h at 25° C
  3. customFinally, the reaction mixture was evaporated to dryness
  4. customThe crude product was purified by chromatography (silica gel; gradient: CH2Cl2 to CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-388fb23388b546459518ec5301951860
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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