Hydrochloric Acid → 2,4-Diamino-1,5-diphenylpentan-3-ol

HRID 847584Notes

Reaction equation

HRID 847584 reaction equation
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:3]([OH:20])[CH:4]([NH:12]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>O1CCOCC1>[NH2:1][CH:2]([CH:3]([OH:20])[CH:4]([NH2:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

Product 1

HCID 46273942,4-Diamino-1,5-diphenylpentan-3-olYield 10%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The resultant compound of Example 11 (18 mg, 0.049 mmol) was treated with 1 ml of 4M HCl in dioxane, stirred for 0.5 h at ambient temperature, and concentrated in vacuo. The residue was partitioned between chloroform and aqueous NaHCO3, dried over Na2SO4 and concentrated to provide the desired compound (Rf 0.12, 10% methanol in chloroform) as a white solid, m.p. 106°-107° C. 1H NMR (CDCl3) δ 2.51 (dd, J=13, 10 Hz, 1H), 2.67 (dd, J=13, 9 Hz, 1H), 2.85-3.0 (m, 2H), 3.19 (m, 1H), 3.38 (m, 2H), 7.15-7.35 (m, 10H). Mass spectrum: (M+H)+ =271.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between chloroform and aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6ff64b51f4234699bfce2653c56c85a9
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

Loading…