Dimedone → HCID 22260507, compound

HRID 1179182Notes

Reaction equation

HRID 1179182 reaction equation
C(O[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:32]#[N:33])([NH:12][C:13](=[O:31])[CH:14]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:8]1)=O)C=C.[CH3:34][C:35]1([CH3:43])[CH2:42]C(=O)[CH2:39][C:37](=[O:38])[CH2:36]1>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:32]([C:9]1([NH:12][C:13]([CH:14]([NH:22][C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:31])[CH2:10][CH2:11][N:7]([C:5]2[CH2:34][C:35]([CH3:43])([CH3:42])[CH2:36][C:37](=[O:38])[CH:39]=2)[CH2:8]1)#[N:33]

Participants

5

Reactant 2

HCID 31358DimedoneHCID 91569723HCID 91569723, compound

Product 1

HCID 22260507HCID 22260507, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Cyano-3-{3-cyclohexyl-2-[(morpholine-4-carbonyl)-amino]-propionylamino}-pyrrolidine-1-carboxylic acid (2-propen-1-yl) ester (1.35 g, 2.93 mmol, 1.00 equiv) was dissolved in 35 mL of CH2Cl2 along with dimedone (3.30 g, 23.5 mmol, 8.03 equiv). Pd(PPh3)4 (0.25 g, 0.22 mmol, 0.07 equiv) was added and the suspension was stirred at room temperature for 3.5 h. The reaction mixture was concentrated and taken up into EtOAc (100 mL) and extracted with 1 N HCl (2×50 mL). Concentration of the organic phase and purification of the crude mixture by reverse-phase HPLC provide the product as two separate diastereomers; MS, m/z 500=M+1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with 1 N HCl (2×50 mL)
  3. customConcentration of the organic phase and purification of the crude mixture by reverse-phase HPLC
  4. customprovide the product as two
  5. customseparate diastereomers

Sources & evidence

ORD record
ord-7e255ffc72b342da9edd817c663c1d36
Source dataset
uspto-grants-2007_10
Patent number
US07279472B2

Reaction notes

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