Dimedone → HCID 22260507, compound

HRID 2229373Notes

Reaction equation

HRID 2229373 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-9469471083ef4187afa0b8b4460482cd
Source dataset
uspto-grants-2002_07
Patent number
US06420364B1

Reaction notes

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