Dicyclohexylcarbodiimide → HCID 86754820, compound

HRID 1603312Notes

Reaction equation

HRID 1603312 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([O:16][C@@H:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:15])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:25]([O:39][C:40]1[CH:48]=[CH:47][C:43]([C:44](O)=[O:45])=[CH:42][CH:41]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C1CCC(N=C=NC2CCCCC2)CC1.CN(C1C=CC=CN=1)C>ClCCl>[CH2:25]([O:39][C:40]1[CH:41]=[CH:42][C:43]([C:44]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:13]=[CH:12][C:11]([C:14]([O:16][C@@H:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:15])=[CH:10][N:9]=3)=[CH:4][CH:3]=2)=[O:45])=[CH:47][CH:48]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 2894104-(Tetradecyloxy)benzoic acidHCID 136340744HCID 136340744, compound

Product 1

HCID 86754820HCID 86754820, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

--The hydroxy ester 60 (410 mg, 1.25 mol), 4-tetradecyloxybenzoic acid (417 mg, 1.25 mmol), DCC (257 mg, 1.25 mmol) and dimethylaminopyridine (cat.) in dry dichloromethane (15 ml) were stirred for 48 h at room temperature. Flash silica was added and the solvent was removed in vacuo and the residue was purified by flash chromatography (10% ethyl acetate-light petroleum) to give the ester 61 (230 mg, 28%) (from EtOH/MeOH), transitions/° C. I TGB(fog) TGB(C or A) SC 88 SCferri1 81.4 SCferri2SCanti 69 K (m.p. 85.4° C.); [α]D19 +20.2° (c 1.9 in CHCl3); νmax /cm-1 (KBr) 2880, 1705 (CO), 1690 (CO), 1610, 1460, 1290, 1240, 1195, 1110 and 830; δ 0.88 (6H, m), 1.20-1.60 (33H, m), 1.60-1.90 (4H, m), 4.05 (2H, t, J 6, OCH2), 5.22 (1H, sext, J 6, OCHMe), 6.98 (2H, J 8, 3'- and 5'-H), 7.37 (2H, d, J 8, ArH), 8.16 (2H, d, J 8, ArH), 8.60(2H, d, J8, 2'- and 6'-H) and 9.31 (2H,s,); m/z 642 (M+ -2), 419,317,265 and 121.

Workup

  1. additionFlash silica was added
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography (10% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-146932631fe346778ce06f2c7e1ab51c
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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