3-Amino-1-propanol → HCID 54004382, compound

HRID 2371979Notes

Reaction equation

HRID 2371979 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([O:8][C:9]([C@@H:11]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:12][C@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](Cl)=[O:15])=[O:10])[CH3:7]>C(Cl)Cl>[CH2:6]([O:8][C:9]([C@@H:11]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:12][C@H:13]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:14]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:15])=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 53863562HCID 53863562, compound

Product 1

HCID 54004382HCID 54004382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 0.52 g of 3-amino-1-propanol in 10 ml of methylene chloride is added 0.5 g of 4-ethoxycarbonyl-2,4-(R*,R*)-dibenzylbutyryl chloride in 10 ml of methylene chloride. The mixture is stirred 10 minutes at room temperature. The reaction mixture is concentrated and diluted with ethyl acetate. The organic portions are washed with 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated to give N-[4-ethoxycarbonyl-2,4-(R*,R*)-dibenzylbutyryl]-3-amino-1-propanol as a colorless oil; NMR (CDCl3) δ7.31 and 7.28 (s, 10H, Ar--H), 5.82 (t, 1H, J=7 Hz, NH), 4.02 (q, 2H, J=8 Hz, OCH2), 3.3-1.25 (m, 15H), 1.10 (t, 3H, J=8 Hz, CH3).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic portions are washed with 1N hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8a9367449acd44a1b37635c36bfab5f2
Source dataset
uspto-grants-1992_03
Patent number
US05096925

Reaction notes

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