(R)-(-)-2-Amino-1-propanol → HCID 66702109, compound

HRID 424679Notes

Reaction equation

HRID 424679 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]([N:15]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C@@H:30]([CH2:32][OH:33])[CH3:31]>>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([N:15]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[C:11]([NH:29][C@H:30]([CH3:31])[CH2:32][OH:33])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 86602821HCID 86602821, compound

Product 1

HCID 66702109HCID 66702109, compound

Conditions

Temperature
80 °C

Procedure

To a solution of the product of step i) (21.2 g) in NM) (40 ml) was added (R)-alaninol (10 g) and the whole heated at 80° C. for 4 h. The reaction mixture was then partitioned between EtOAc and H2O. The organic phase was collected, dried (MgSO4) and the solvent removed to leave a pale yellow oil. This was purified by silica gel chromatography (60:40 iso-hexane/EtOAc) to afford the subtitle compound as a colourless oil. Yield: 13.9 g.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and H2O
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed
  5. customto leave a pale yellow oil
  6. customThis was purified by silica gel chromatography (60:40 iso-hexane/EtOAc)

Sources & evidence

ORD record
ord-70d8643c26df4947870907901b86bdf0
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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