Dicyclohexylcarbodiimide → HCID 52933495, compound

HRID 574058Notes

Reaction equation

HRID 574058 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([O:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:52]1(=[O:58])[NH:56][C:55](=[O:57])[CH:54]=[CH:53]1>C1COCC1.CN(C1C=CN=CC=1)C.CCOCC>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([O:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:56]3[C:52](=[O:58])[CH:53]=[CH:54][C:55]3=[O:57])=[O:17])=[CH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10935MaleimideHCID 52933493HCID 52933493, compound

Product 1

HCID 52933495HCID 52933495, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trityl acid 8 (280 mg, 0.42 mM) in dry THF (6 mL) was added dicyclohexyl carbodiimide (DDC, 400 mg, 1.95 mM). The reaction mixture was stirred for 30 min at r.t., and maleimide (100 mg, 1.1 mM) and a catalytic amount of DMAP was added and allowed to stir for overnight. The solvent was removed under rotaevaporator and the solid obtained was dissolved in dry ether. The precipitated DCU was filtered and the solvent ether was evaporated. Part of the product was purified by preparative TLC. Yield: 12 mg. 1H-NMR (500 MHz, CDCl3) δ ppm: 1.78 (m, 2H), 1.95 (m 2H), 2.9 (s, 4H), 3.51 (m, 2H), 3.93 (t, 2H), 4.02 (t, 2H), 6.8 (m, 5H), 7.25 (m, 5H), 7.29 (m, 5H), 7.37 (m, 3H), 7.48 (d, 2H), Mass: 561.3 (M+).

Workup

  1. stirringto stir for overnight
  2. customThe solvent was removed under rotaevaporator
  3. customthe solid obtained
  4. filtrationThe precipitated DCU was filtered
  5. customthe solvent ether was evaporated
  6. customPart of the product was purified by preparative TLC

Sources & evidence

ORD record
ord-fbcc553f5b6546e9a4bfe7d162f79b7a
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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