Trityl chloride → HCID 86592184, compound

HRID 1246687Notes

Reaction equation

HRID 1246687 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([NH:15][NH2:16])=[O:14])[CH:6]=[C:7]([CH:12]=1)[C:8]([NH:10][NH2:11])=[O:9].C(N[CH:21]([CH3:23])[CH3:22])(C)C.[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[C:24]([NH:11][NH:10][C:8](=[O:9])[C:7]1[CH:12]=[C:3]([CH2:2][OH:1])[CH:4]=[C:5]([C:13]([NH:15][NH:16][C:24]([C:22]2[CH:21]=[CH:23][CH:42]=[CH:37][CH:38]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:14])[CH:6]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 7912DiisopropylamineHCID 69302191HCID 69302191, compound

Product 1

HCID 86592184HCID 86592184, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.0 g (8.92 mmol) of dihydrazide 2 in 20 ml of DMF was added 9.1 ml (53.5 mmol) of diisopropylamine and 5.6 g (19.6 mmol) of trityl chloride. The mixture was stirred for 2.5 hours, concentrated, and crystallized in 100 ml ethyl acetate. The product was filtered, washed with cold ethanol, dried under low vacuum at 40° C. for 18 h o yield 5.2 g (82%) of 3: 1H-NMR (DMSO-d6,) 9.36 (d, J=7.4 Hz, 2H), 7.47–7.17 (m, 33H), 6.12 (d, J=7.4 Hz, 2H), 5.28 (t, J=5.7 Hz, 1H), 4.41 (d, J=5.7 Hz); 13C-NMR 165.4, 144.3, 142.5, 132.6, 128.5, 127.7, 126.8, 124.6, 73.4, 62.1.

Workup

  1. concentrationconcentrated
  2. customcrystallized in 100 ml ethyl acetate
  3. filtrationThe product was filtered
  4. washwashed with cold ethanol
  5. dry with materialdried under low vacuum at 40° C. for 18 h o yield 5.2 g (82%) of 3

Sources & evidence

ORD record
ord-c216b8a406f14f2f84e0e7ab1209d02f
Source dataset
uspto-grants-2006_10
Patent number
US07129229B2

Reaction notes

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