Phosphate → HCID 19829883, compound

HRID 1493631Notes

Reaction equation

HRID 1493631 reaction equation
C[O-].[Na+].NC(N)=O.[NH2:8][C:9]([NH:11][N:12]([CH2:26][C:27]([O:29]C)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:14]=1)=[O:10].P([O-])([O-])([O-])=O>COCCOC.CCCCCC.CCOCC>[CH2:20]([O:19][C:15]1[CH:14]=[C:13]([N:12]2[CH2:26][C:27](=[O:29])[NH:8][C:9](=[O:10])[NH:11]2)[CH:18]=[CH:17][CH:16]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 1176UreaHCID 10942334Sodium MethoxideHCID 53682015HCID 53682015, compound

Product 1

HCID 19829883HCID 19829883, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 21584099Diethylether hexaneSolvent

Procedure

Sodium methoxide (0.33 g, 6.2 mmol) was added under nitrogen to a stirred solution of the urea (Intermediate 70, 1.00 g, 3.1 mmol) in 1,2-dimethoxyethane (25 ml) over 4 A° molecular sieves. After 15 minutes the mixture was poured into pH6.5 aqueous phosphate buffer (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were dried (MgSO4) and evaporated to afford the crude product as an off-white solid. Trituration with hexane/ether (ca. 1:2) (25 ml) gave the title compound as a white powder (600 mg, 67%) m.p. 161°-163° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customto afford the crude product as an off-white solid

Sources & evidence

ORD record
ord-0ed14782a9ba45d3bcfa78b4fda5b37a
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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