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

HRID 2165301Notes

Reaction equation

HRID 2165301 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) δ 7.31 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-c2b48bf122c448bab6747c4248d362fe
Source dataset
uspto-grants-1990_07
Patent number
US04939261

Reaction notes

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