Trityl chloride → HCID 10374484, compound

HRID 1585147Notes

Reaction equation

HRID 1585147 reaction equation
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[C:14](Cl)(C1C=CC=CC=1)([C:21]1C=CC=CC=1)[C:15]1C=CC=CC=1>C(Cl)Cl>[CH3:4][C:3]1([CH3:5])[CH2:2][NH:1][CH2:15][C@@H:14]([CH3:21])[NH:6]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 131282-Methylpropylenediamine

Product 1

HCID 10374484HCID 10374484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1,2-diamino-2-methylpropane (XXVI, 10 ml) and triethylamine (20 ml) in methylene chloride (400 ml) is cooled to -40°. Trityl chloride (26 g) in methylene chloride (75 ml) is added dropwise and the reaction is allowed to warm to 20-25° and stir for 40 h. After a standard basic workup (methylene chloride, sodium bicarbonate and magnesium sulfate) the residue is chromatographed (silica gel; ethyl acetate/methanol, 9/1), to provide the desired compound, mp 97-98°; IR (mineral oil) 2956, 2925, 2869, 2855, 1487, 1462, 1449, 747 and 708 cm-1 ; NMR (CDCl3) 7.51, 7.27, 7.17, 1.94-2.01, 1.71-1.82 and 1.12 δ; MS (m/e) 273, 258, 243, 165 and 58.

Workup

  1. temperatureis cooled to -40°
  2. temperatureto warm to 20-25°
  3. customAfter a standard basic workup (methylene chloride, sodium bicarbonate and magnesium sulfate) the residue is chromatographed (silica gel; ethyl acetate/methanol, 9/1)

Sources & evidence

ORD record
ord-467480e1fbc14558a2ca958e2e728877
Source dataset
uspto-grants-1999_08
Patent number
US05935970

Reaction notes

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