Trityl chloride → HCID 14258586, compound

HRID 1466544

Reaction equation

HRID 1466544 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][C@H:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(N(CC)CC)C>ClCCl>[C:1]([NH:22][C@H:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 208636Di-tert-butyl glutamate hydrochloride

Product 1

HCID 14258586HCID 14258586, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tritylchloride (2.05 g. 7.36 mmol) was added to a solution of di-tert-butyl L-glutamate hydrochloride (2.15 g, 7.27 mmol) and triethylamine (5 mL, 36 mmol) in dichloromethane (20 mL). The solution was stirred for overnight (16 h) at room temperature. The solution was washed with sodium bicarbonate solution (3×10 mL) and water (2×5 mL). After drying over sodium sulphate, the solvent was evaporated. The crude product was purified by flash chromatography (ethyl acetate/n-hexane: 2/98 to 3/97) to give di-tert-butyl N-trityl-L-glutamate (3.2 g, 88%) as a white foam.

Workup

  1. washThe solution was washed with sodium bicarbonate solution (3×10 mL) and water (2×5 mL)
  2. dry with materialAfter drying over sodium sulphate
  3. customthe solvent was evaporated
  4. customThe crude product was purified by flash chromatography (ethyl acetate/n-hexane: 2/98 to 3/97)

Sources & evidence

ORD record
ord-57908132bf3942c3af79d58e770666e3
Source dataset
uspto-grants-2015_04
Patent number
US09000037B2

Linked notes

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