Propionic Acid → HCID 12052616, compound

HRID 1936919Notes

Reaction equation

HRID 1936919 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:41])[CH2:39][CH3:40]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]1(/[CH:11]=[C:12]2/[CH:13]([O:22][C:38](=[O:41])[CH2:39][CH3:40])[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 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 12052610HCID 12052610, compound

Product 1

HCID 12052616HCID 12052616, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

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 propionic acid (3.8 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 8.3 mg (69 percent) of Compound 36: pale yellow oil; Rf=0.43 (20 percent EtOAc in hexane); IR (neat) 2958, 2235, 1726, 1189, 1067 cm−1; 1H NMR (300 MHz, CDCl3) δ8.31 (d, J=7.23 Hz, 1H), 8.01 (d, J=7.56 Hz, 1H), 7.83 (t, J=8.01 Hz, 2H), 7.54-7.46 (m, 3H), 7.45 (s, 1H), 6.24 (s, 1H), 2.52-2.24 (m, 6H), 1.96-1.67 (m, 4H), 1.20 (t, J=7.56 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ174.5, 134.2, 133.0, 132.7, 132.2, 129.7, 129.3, 127.0, 127.0, 126.5, 126.0, 124.2, 123.8, 103.3, 93.6, 81.0, 79.5, 69.4, 28.5, 28.3, 28.2, 22.6, 21.5, 9.8; MS (+CI) m/z (relative intensity) 342 (M+, 5), 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-c873f1510db34ce287e75ab337864d9a
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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