Triethylamine → HCID 15221586, compound

HRID 726532Notes

Reaction equation

HRID 726532 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][C:12]=1[NH2:24])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CC[C:27]([C:29](Cl)=[O:30])=[O:28].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][P:4]([CH2:9][N:10]1[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][C:12]=2[NH:24][C:27](=[O:28])[C:29]1=[O:30])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11007880Butanoyl chloride, 2-oxo-HCID 23196366HCID 23196366, compound

Product 1

HCID 15221586HCID 15221586, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of (2-amino-4-nitro-1-naphthylamino)-methanephosphonic acid diethyl ester is dissolved in a few ml of tetrahydrofuran and treated with 95 microliters of distilled ethyloxalyl chloride and 118 microliters of triethylamine at ice-bath temperature. The solution is stirred first to room temperature and then the reaction is allowed to be completed at 55° oil bath temperature. The batch is concentrated by evaporation, taken up in ethyl acetate and washed with brine, dried and spun in. The crude product is chromatographed on silica gel with ethanol as mobile solvent. 76 mg or 67% of theory of product is obtained as polar fraction. NMR (DMSO,Delta in ppm): 1.03 (6H tr), 3.8 (4H dq), 4.93 (2H d), 7.73 (2H dd), 8.2, 8.35, 8.47 each 1H.

Workup

  1. customto be completed at 55°
  2. concentrationThe batch is concentrated by evaporation
  3. washwashed with brine
  4. customdried
  5. customThe crude product is chromatographed on silica gel with ethanol as mobile solvent
  6. custom76 mg or 67% of theory of product is obtained as polar fraction

Sources & evidence

ORD record
ord-edc251597b5349049dcd41846c79e5be
Source dataset
uspto-grants-1998_01
Patent number
US05710138

Reaction notes

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