Dicyclohexylcarbodiimide → HCID 12052612, compound

HRID 1936922Notes

Reaction equation

HRID 1936922 reaction equation
[C:1]1(/[CH:11]=[C:12]2/[CH:13]([OH:22])[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21]/2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:38][O:39][C:40]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:41]=1[C:42](O)=[O:43]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]1(/[CH:11]=[C:12]2/[CH:13]([O:22][C:42](=[O:43])[C:41]3[CH:45]=[C:46]([O:49][CH3:50])[CH:47]=[CH:48][C:40]=3[O:39][CH3:38])[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21]/2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 760272,5-Dimethoxybenzoic acidHCID 12052610HCID 12052610, compound

Product 1

HCID 12052612HCID 12052612, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 20b (18.6 mg, 6.50×10−2 mmol), DCC (13.4 mg, 6.50×1031 2 mmol), and DMAP (15.8 mg, 0.13 mmol) in dry CH2Cl2 (4 mL) cooled in an ice-water bath was added 2,5-dimethoxybenzoic acid (17.8 mg, 9.76×10−2 mmol) followed by stirring at room temperature for 24 hours. The reaction mixture was filtered through a short plug of Celite with rinsing by EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 21.7 mg (74 percent) of Compound 40: pale yellow oil; Rf32 0.33 (20 percent EtOAc in hexane); IR (neat) 2958, 2235, 1721, 1640, 1189, 1064 cm−1; 1H NMR (300 MHz, CDCl3) δ8.32 (d, J=7.26 Hz, 1H), 8.08-8.04 (m, 1H), 7.88-7.78 (m, 2H), 7.60 (s, 1H), 7.54-7.42 (m, 4H), 7.03 (dd, J=9.03 and 3.39 Hz, 1H), 6.92 (d, J=9.03 Hz, 1H), 6.45 (s, 1 H), 3.84 (s, 3H), 3.80 (s, 3H), 2.46-2.25 (m, 4H), 1.95-1.70 (m, 4H); 13C NMR (75 MHz, CDCl3) δ169.9, 154.5, 153.7, 134.2, 133.3, 132.2, 129.5, 129.2, 127.0, 126.9, 126.4, 126.0, 124.3, 123.7, 120.3, 117.1, 114.6, 103.1, 93.5, 81.0, 79.5, 69.6, 57.6, 56.6, 28.3, 28.1, 22.6, 21.5; MS (+CI) m/z (relative intensity) 451 (M+, 3), 164 (100).

Workup

  1. filtrationThe reaction mixture was filtered through a short plug of Celite
  2. washwith rinsing by EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

Sources & evidence

ORD record
ord-8c370dab82454706bb94082bd3c45efb
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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