Water → HCID 86602454, compound

HRID 1455009Notes

Reaction equation

HRID 1455009 reaction equation
[NH2:1][C@@H:2]([CH2:4][OH:5])C.[Cl:6][C:7]1[N:12]=[C:11](Cl)[C:10]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[C:9]([Cl:19])[N:8]=1.C(N(CC)CC)C.[OH2:27]>CN(C=O)C.CCOC(C)=O>[Cl:6][C:7]1[N:8]=[C:9]([Cl:19])[C:10]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[C:11]([NH:1][C@H:2]([OH:27])[CH2:4][OH:5])[N:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 85945614HCID 85945614, compound

Product 1

HCID 86602454HCID 86602454, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-alaninol (0.46 g) in DMF (20 ml) was added dropwise to the subtitle product of step iii) (1.60 g) at −5° C. To this mixture was added triethylamine (0.63 g), the mixture allowed to come to room temperature and stirred for 1 h. To the mixture was added water (60 ml) and EtOAc (2×200 ml). The organic layer was washed With water (3×50 ml), brine (30 ml) and dried (MgSO4). The solid was filtered and the filtrate evaporated to dryness to give a yellow solid. This was chromatographed using EtOAc as eluent to yield the subtitle compound.

Workup

  1. customto come to room temperature
  2. washThe organic layer was washed With water (3×50 ml), brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationThe solid was filtered
  5. customthe filtrate evaporated to dryness
  6. customto give a yellow solid
  7. customThis was chromatographed

Sources & evidence

ORD record
ord-2bd6445fec0349ae8caea138d194cc61
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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