Dicyclohexylcarbodiimide → HCID 52933494, compound

HRID 574057Notes

Reaction equation

HRID 574057 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]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1.C1(N=C=NC2CCCCC2)CCCCC1.O[N:53]1[C:57](=[O:58])[CH2:56][CH2:55][C:54]1=[O:59]>C1COCC1.CN(C1C=CN=CC=1)C.CCOCC>[O:59]=[C:54]1[CH2:55][CH2:56][C:57](=[O:58])[N:53]1[O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:12]([C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][CH2:2][OH:1])[CH:6]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 52933493HCID 52933493, compound

Product 1

HCID 52933494HCID 52933494, compound

Reagents, catalysts & solvents 3

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

Procedure

To a stirred solution of trityl acid 8 (200 mg, 0.42 mM) in dry THF (6 mL) was added dicyclohexyl carbodiimide (DDC, 206 mg, 1 mM). The reaction mixture was stirred for 30 min at r.t., and N-hydroxysuccinimide (70 mg, 0.6 mM) and a catalytic amount of DMAP added and was 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. The crude solid obtained was separated by silica column chromatography using CH2Cl2. Yield: about 120 mg. 1H-NMR (500 MHz, CDCl3) δ ppm: 1.70 (m, 2H), 1.9 (t, 2H), 2.9 (s, 4H), 3.5 (m, 2H), 3.9 (t, 2H), 4.0 (t, 2H), 6.85 (m, 4H), 7.25 (m, 4H), 7.32 (m, 5H), 7.51 (m, 3H), 8.09 (d, 2H).

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. customThe crude solid obtained
  7. customwas separated by silica column chromatography

Sources & evidence

ORD record
ord-e5cc985fb7f545eca690cc2d41da2f07
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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