(R)-(-)-2-Amino-1-propanol → HCID 10155773, compound

HRID 968216Notes

Reaction equation

HRID 968216 reaction equation
Cl[C:2]1[C:3]2[CH2:20][C:19](=[O:21])[NH:18][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1.[NH2:22][C@H:23]([CH3:26])[CH2:24][OH:25]>CN1C(=O)CCC1>[F:17][C:11]1[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][S:8][C:6]1[N:7]=[C:2]([NH:22][C@H:23]([CH3:26])[CH2:24][OH:25])[C:3]2[CH2:20][C:19](=[O:21])[NH:18][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 15896315HCID 15896315, compound

Product 1

HCID 10155773HCID 10155773, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

The product from example 1, step (e) (0.20 g) in NMP (5 ml) was treated with (R)-2-amino-1-propanol (0.56 g) and the reaction mixture was heated at 110° C. for 2 hours. The mixture was evaporated to dryness and the residue purified (HPLC, Symmetry® C18 column, 0.1% aqueous ammonium acetate:acetonitrile isocratic elution 75:25) to afford the title compound (0.055 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue purified
  3. wash(HPLC, Symmetry® C18 column, 0.1% aqueous ammonium acetate:acetonitrile isocratic elution 75:25)

Sources & evidence

ORD record
ord-ea28dccc9a694ae39484d72a2fa63db8
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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