Acetone → HCID 24898188, compound

HRID 2358627Notes

Reaction equation

HRID 2358627 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:35](CC)[C:36]([O-:38])=[O:37].[CH3:41][C:42](C)=O>>[CH2:41]([O:38][C:36](=[O:37])[CH2:35][O:15][C:12]1[CH:11]=[CH:10][C:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=2[NH:16][C:17]2[C:26]3[C:21](=[N:22][C:23]([CH3:27])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)=[CH:14][CH:13]=1)[CH3:42]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 1523172-BromobutyrateHCID 24897972HCID 24897972, compound

Product 1

HCID 24898188HCID 24898188, compound

Procedure

Material from Example 5 (0.200 g, 0.536 mmol) was suspended in acetone to which K2CO3 was added. This was treated with bromo-ethyl-acetate (0.089 g, 0.536 mmol) at which time the reaction mixture was heated to reflux for 4 hrs. Reaction mixture cooled to room temperature, solid filtered and concentrated under vacuum giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (24 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.22 (t, J=6.99 Hz, 3H), 2.34 (s, 3H), 2.74 (s, 3H), 4.20 (q, J=6.99 Hz, 2H), 5.47 (s, 2H), 6.49 (d, J=7.72 Hz, 1H), 6.75 (d, J=8.82 Hz, 2H), 7.00 (d, J=8.09 Hz, 1H), 7.20 (d, J=8.46 Hz, 2H), 7.25-7.40 (m, 2H), 7.87 (d, J=8.82 Hz, 1H), 8.63 (d, J=7.72 Hz, 1H), 9.06 (d, J=8.46 Hz, 1H), 9.89 (s, 1H); MS(ESI) m/z 460 (M+H)+, (ESI−) m/z 458 (M−H)−.

Workup

  1. additionwas added
  2. temperaturewas heated
  3. temperatureto reflux for 4 hrs
  4. customReaction mixture
  5. filtrationsolid filtered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aad645ea041a41ddbf1a91f54045f46a
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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