Trityl chloride → HCID 59827592, compound

HRID 1363861Notes

Reaction equation

HRID 1363861 reaction equation
Cl.Cl.[CH3:3][O:4][CH2:5][CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1.C(N(CC)CC)C.[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:3][O:4][CH2:5][CH:6]1[CH2:11][N:10]([C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:9][CH2:8][NH:7]1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 66941255HCID 66941255, compound

Product 1

HCID 59827592HCID 59827592, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 12 (2.14 g, 10.5 mmol) was dissolved in dry CH2Cl2 (60 ml), in the presence of dry triethylamine (5.9 ml, 42.3 mmol). The solution was cooled (0° C.) and triphenylmethyl chloride (2.94 g, 10.6 mmol) in dry CH2Cl2 (10 ml) was added drop-wise. Once the addition was complete the reaction was warmed to room temperature and stirred for 16 h. The reaction mixture was washed with saturated NaHCO3 (75 mL), water (75 mL), and brine (75 mL). The organic portion was dried (K2CO3), and concentrated in vacuo to give 13 as an amorphous foam (3.96 g, 99% yield). 1H NMR (400 MHz, CDCl3): δ 1.3 (m, 3H), 1.9 (s, 3H), 3.0 (m, 3H), 3.2 (m, 1H), 3.3 (s, 3H), 7.16 (m, 4H), 7.27 (m, 7H), 7.49 (m, 4H).

Workup

  1. additionwas added drop-wise
  2. additionOnce the addition
  3. washThe reaction mixture was washed with saturated NaHCO3 (75 mL), water (75 mL), and brine (75 mL)
  4. dry with materialThe organic portion was dried (K2CO3)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76ee61dd273c44228f2772b0ed91a923
Source dataset
uspto-grants-2011_02
Patent number
US07887784B2

Reaction notes

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