Serinol → HCID 86726488, compound

HRID 1487656Notes

Reaction equation

HRID 1487656 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].CCN(C(C)C)C(C)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[N+:27]([O-:29])=[O:28])[C:21](Cl)=[O:22]>O1CCOCC1>[OH:4][CH2:3][CH:2]([NH:1][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:26]([N+:27]([O-:29])=[O:28])=[C:18]([O:17][CH3:16])[CH:19]=1)[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 68294SerinolHCID 81531DiisopropylethylamineHCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 86726488HCID 86726488, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of 2-amino-propane-1,3-diol (1 equiv) in 1,4-dioxane (0.062 M) was added DIEA (2 equiv) and a solution of 3-methoxy-4-nitrobenzoyl chloride (1 equiv) in 1,4-dioxane (1.86 M) dropwise at room temperature. The resulting mixture was stirred at room temperature for 15 min. The solution was concentrated and the crude material was triturated in a 5:1 mixture of water:DCM (0.5 M), filtered, and dried to afford the title compound the solid (85% yield) that was used in the next step without further purification. MS (ESI) m/z 271.1 [M+H]+.

Workup

  1. customdropwise at room temperature
  2. concentrationThe solution was concentrated
  3. customthe crude material was triturated in a 5:1 mixture of water
  4. filtrationDCM (0.5 M), filtered
  5. customdried

Sources & evidence

ORD record
ord-5ce9ee1c2d3444018d538513433185de
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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