Octanoic Acid → HCID 12052617, compound

HRID 1936920Notes

Reaction equation

HRID 1936920 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.[C:38](O)(=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>CN(C1C=CN=CC=1)C>[C:1]1(/[CH:11]=[C:12]2/[CH:13]([O:22][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[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

5

Reactant 3

HCID 379Octanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 12052610HCID 12052610, compound

Product 1

HCID 12052617HCID 12052617, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of Compound 20b (10.0 mg, 3.50×10−2 mmol), DCC (7.2 mg, 3.50×10−2 mmol), and DMAP (8.5 mg, 6.99×10−2 mmol) in dry Ch2Cl2 (4 mL) cooled in an ice-water bath was added n-octanoic acid (7.5 mg, 5.24×10−2 mmol) followed by stirring at room temperature for 4 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 11.2 mg (78 percent) of Compound 37: pale yellow oil; Rf=0.65 (20 percent EtOAc in hexane); IR (neat) 2932, 1724, 1177, 1037 cm−1; 1H NMR (300 MHz, CDCl3) δ8.31 (d, J=7.26 Hz, 1H), 8.01 (d, J=7.41 Hz, 1H), 7.86-7.78 (m, 2H), 7.56-7.46 (m, 3H), 7.44 (s, 1H), 6.24 (s, 1H), 2.54-2.22 (m, 4H), 2.42 (t, J=7.53 Hz, 2H), 1.97-1.60 (m, 6H), 1.40-1.16 (m, 8H), 0.84 (t, J=7.02 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ173.9, 134.2, 133.0, 132.7, 132.2, 129.6, 129.3, 127.0, 127.0, 126.5, 126.0, 124.2, 123.8, 103.2, 93.6, 80.9, 79.5, 69.2, 35.2, 32.3, 29.7, 29.6, 28.3, 28.2, 25.7, 23.3, 22.6, 21.4, 14.7; MS (+CI) m/z (relative intensity) 413 (M+, 6), 269 (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-f86edf81cb2144918f564c5f74d4ad3e
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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