Theobromine → (+/-)-2-[2-(3,7-Dimethylxanthin-1-yl)ethyl]-n-methyl-n-(4-phenoxybenzene-sulfonyl)glycine allyl ester

HRID 1838423Notes

Reaction equation

HRID 1838423 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH3:11])[C:6]=2[C:5](=[O:12])[NH:4][C:3]1=[O:13].[H-].[Na+].[CH2:16]([O:19][C:20](=[O:43])[CH:21]([CH2:40][CH2:41]Br)[N:22]([CH3:39])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:17]=[CH2:18].[Cl-].[NH4+]>CN(C)C=O>[CH2:16]([O:19][C:20](=[O:43])[CH:21]([CH2:40][CH2:41][N:4]1[C:5](=[O:12])[C:6]2[N:7]([CH3:11])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:13])[N:22]([CH3:39])[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 5429TheobromineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18753632(+/-)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester

Product 1

HCID 18753500(+/-)-2-[2-(3,7-Dimethylxanthin-1-yl)ethyl]-n-methyl-n-(4-phenoxybenzene-sulfonyl)glycine allyl esterYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

After addition of 3,7-dimethylxanthin (1.10 g, 6.1 mmol) to a suspension of sodium hydride (60%, 0.24 g, 6.0 mmol) in N,N-dimethylformamide (20 ml), the mixture was stirred at 50° C. for 2 hours. After cooling it to room temperature, a solution of (±)-2-(2-bromoethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester (2.34 g, 5.0 mmol) in N,N-dimethylformamide (10 ml) was added to the reaction mixture. This was heated at 80° C. for 2 hours. After cooling it to room temperature, a saturated aqueous solution of ammonium chloride was added and then this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate 3/1 as the eluant to afford the desired compound (0.86 g, yield 30%) as a colorless amorphous solid.

Workup

  1. temperatureAfter cooling it to room temperature
  2. temperatureThis was heated at 80° C. for 2 hours
  3. temperatureAfter cooling it to room temperature
  4. extractionthis was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ac727818fd294cfba28849e733be6550
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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