Potassium Phosphate, Tribasic → HCID 21622017, compound

HRID 257597Notes

Reaction equation

HRID 257597 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:16]([O:30][CH2:31][CH3:32])[C:17]3[C:22]([O:23][C:24]=2[CH:25]=1)=[CH:21][C:20]([O:26][C:27](=[O:29])[CH3:28])=[CH:19][CH:18]=3)(=[O:10])[CH3:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl>[C:27]([O:26][C:20]1[CH:19]=[CH:18][C:17]2[C:16]([CH2:4][CH2:3][C:2]([N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)=[O:1])([O:30][CH2:31][CH3:32])[C:15]3[C:24]([O:23][C:22]=2[CH:21]=1)=[CH:25][C:12]([O:11][C:8](=[O:10])[CH3:9])=[CH:13][CH:14]=3)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 79341Piperidin-4-olHCID 19958012HCID 19958012, compound

Product 1

HCID 21622017HCID 21622017, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxypiperidine (506 mg, 5.00 mmol, 2.5 eq, Aldrich) and 9-(2-(N-succinimidyloxy-carbonyl))ethyl)-3,6-diacetoxy-9-ethoxy-9H-xanthene, 7a (1.023 g, 2.00 mmol, prepared according to Prober, et al., EP-A 252,683) in dry dichloromethane (20 ml) was stirred for 30 min. The reaction was added to 1M aqueous potassium phosphate buffer (30 mL; pH =7) and extracted with dichloromethane (3×30 mL). The organic extracts were dried over calcium sulfate, concentrated, and dried under vacuum overnight to afford crude amide 8a (1.039 g, 104%) as an off-white foam. This material was >90% pure according to NMR and TLC and was used without further purification in the next step.

Workup

  1. extractionpH =7) and extracted with dichloromethane (3×30 mL)
  2. dry with materialThe organic extracts were dried over calcium sulfate
  3. concentrationconcentrated
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-af41ad185e0f4f91b3ca24fd9d0ff21a
Source dataset
uspto-grants-1993_11
Patent number
US05262536

Reaction notes

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