Methyl 2-chloroacetoacetate → HCID 58762430, compound

HRID 858879Notes

Reaction equation

HRID 858879 reaction equation
[CH:1]1([C:6](=[O:19])[CH2:7][CH2:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(=O)CCC#CC2C=C(C)C(O)=CC=2C)CCCC1.[Cl:40][CH:41]([C:46]([CH3:48])=[O:47])[C:42](OC)=[O:43]>>[Cl:40][CH:41]1[C:42](=[O:43])[O:19][C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:18])[CH2:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH2:48][C:46]1=[O:47]

Participants

4

Reactant 3

HCID 107332Methyl 2-chloroacetoacetateHCID 587625021-Cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-oneHCID 58762649HCID 58762649, compound

Product 1

HCID 58762430HCID 58762430, compound

Procedure

The desired product was prepared analogously to example F(1), Step 2, substituting N-(3-cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide (300 mg, 1.1 mmol) from Step 2 above in place of 1-cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-one and methyl 2-chloroacetoacetate (0.7 mL, 5.7 mmol) in place of methyl acetoacetate. Yield: 103 mg, 14%.

Sources & evidence

ORD record
ord-7ceb2146659b4a63a27fde9c4efa81c1
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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