4-Nitrobenzoic Acid → (S)-7-benzyl-1-(5-(4-nitrobenzoyloxy)hexyl)-3-methylxanthine

HRID 1814975Notes

Reaction equation

HRID 1814975 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([N:20]1[C:28]2[C:27](=[O:29])[N:26]([CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]([OH:36])[CH3:35])[C:25](=[O:37])[N:24]([CH3:38])[C:23]=2[N:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:39]([C:42]1[CH:50]=[CH:49][C:45]([C:46](O)=[O:47])=[CH:44][CH:43]=1)([O-:41])=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([N:20]1[C:28]2[C:27](=[O:29])[N:26]([CH2:30][CH2:31][CH2:32][CH2:33][C@@H:34]([O:36][C:46](=[O:47])[C:45]3[CH:44]=[CH:43][C:42]([N+:39]([O-:41])=[O:40])=[CH:50][CH:49]=3)[CH3:35])[C:25](=[O:37])[N:24]([CH3:38])[C:23]=2[N:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9885048(R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine

Product 1

HCID 53988311(S)-7-benzyl-1-(5-(4-nitrobenzoyloxy)hexyl)-3-methylxanthineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (14.63 g, 84 mmol) was added dropwise to a solution of (R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine (as prepared in Example 29) (20 g, 56 mmol), 4-nitrobenzoic acid (14 g, 84 mmol) and triphenylphosphine (22 g, 84 mmol) in tetrahydrofuran (200 ml). After stirring for 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 30% ethyl acetate-hexane to provide (S)-7-benzyl-1-(5-(4-nitrobenzoyloxy)hexyl)-3-methylxanthine (25 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-6a8ceb16a3044754822310254f86a316
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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