Diethylphosphite → HCID 53765329, compound

HRID 376736Notes

Reaction equation

HRID 376736 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][C:14]([NH:16][C:17]1[C:18](Br)=[CH:19][C:20]2[C:24]3[CH:25]=[C:26](Br)[C:27]([NH:29][C:30](=[O:44])[CH:31]=[CH:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[C:34]=4[Cl:43])=[CH:28][C:23]=3[S:22](=[O:47])(=[O:46])[C:21]=2[CH:48]=1)=[O:15].C([O:52][P:53]([O-:57])[O:54][CH2:55][CH3:56])C>C(N(CC)CC)C>[CH2:55]([O:54][P:53]([C:18]1[C:17]([NH:16][C:14](=[O:15])[CH:13]=[CH:12][C:3]2[CH:4]=[CH:5][C:6]([O:10][CH3:11])=[C:7]([O:8][CH3:9])[C:2]=2[Cl:1])=[CH:48][C:21]2[S:22](=[O:46])(=[O:47])[C:23]3[CH:28]=[C:27]([NH:29][C:30](=[O:44])[CH:31]=[CH:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[C:34]=4[Cl:43])[C:26]([P:53]([O:54][CH2:55][CH3:56])([OH:52])=[O:57])=[CH:25][C:24]=3[C:20]=2[CH:19]=1)(=[O:52])[OH:57])[CH3:56]

Participants

4

Reactant 2

HCID 3780918DiethylphosphiteHCID 86755107HCID 86755107, compound

Product 1

HCID 53765329HCID 53765329, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To a nitrogen flushed flask containing 2.45 g of the product of Example 16 was added, via syringe, 1.04 ml of diethylphosphite, 1.12 ml of triethylamine and 15 ml of N,N-dimethylformamide(DMF). The resulting stirred mixture was heated to 90° C. and 1.66 g of tetrakistriphenylphosphine palladium(0) was added, rapidly. The reaction was cooled, and the product precipitated by the addition of excess (200 ml) of 1N hydrochloric acid. The solid was collected, washed and lip dried in vacuo. The collected solid was dissolved in acetone; dry Silica Gel was added and the solvent was removed in vacuo. The Silica Gel/compound support was applied to a Silica Gel column which was eluted with 20% acetone, 79% hexane, 1% glacial acetic acid gradient to 50% acetone, 49% hexane, 1% glacial acetic acid). The product containing fractions were combined and concentrated in vacuo to give [3,7-bis-[3-(2-chloro-3,4-dimethoxyphenyl)acryloylamino]-8-(ethoxyhydroxyphosphoryl)-5,5-dioxo-5H-5λ6 -dibenzothiophen-2-yl]-phosphonic acid monoethyl ester.

Workup

  1. additionwas added, via syringe
  2. temperatureThe reaction was cooled
  3. customthe product precipitated by the addition of excess (200 ml) of 1N hydrochloric acid
  4. customThe solid was collected
  5. washwashed
  6. customlip dried in vacuo
  7. dissolutionThe collected solid was dissolved in acetone
  8. additiondry Silica Gel was added
  9. customthe solvent was removed in vacuo
  10. washwas eluted with 20% acetone, 79% hexane, 1% glacial acetic acid gradient to 50% acetone, 49% hexane, 1% glacial acetic acid)
  11. additionThe product containing fractions
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24ee13f3c0ca4a8aad18b363a33b95e9
Source dataset
uspto-grants-2000_02
Patent number
US06022307

Reaction notes

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