Dicyclohexylcarbodiimide → HCID 10381849, compound

HRID 1936918Notes

Reaction equation

HRID 1936918 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[O:39][CH2:40][C:41](O)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:40]([O:22][CH:13]1[C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21]/[C:12]/1=[CH:11]\[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:39])[CH3:41]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12251Methoxyacetic AcidHCID 12052610HCID 12052610, compound

Product 1

HCID 10381849HCID 10381849, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 20b (37 mg, 0.13 mmol), DCC (26.7 mg, 0.13 mmol), and DMAP (31.6 mg, 0.26 mmol) in dry CH2Cl2 (20 mL) cooled in an ice-water bath was added methoxyacetic acid (17.5 mg, 0.19 mmol) followed by stirring at room temperature for 2 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 30.1 mg (65 percent) of Compound 30b: pale yellow oil; Rf=0.38 (20 percent EtOAc in hexane); IR (neat) 2932, 2239,2229, 1756, 1182, 1126 cm−1; 1H NMR (300 MHz, CDCl3) δ8.32 (d, J=7.29 Hz, 1H), 8.14-8.00 (m, 1H), 7.92-7.81 (m, 2H), 7.58-7.44 (m, 3H), 7.50 (s, 1H), 6.33 (t, J=1.05 Hz, 1H), 4.15 and 4.13 (AB q, J=16.50 Hz, 2H), 3.48 (s, 3H), 2.55-2.20 (m, 4H), 2.00-1.60 (m, 4H); 13C NMR (75 MHz, CDCl3) δ170.4, 134.2, 133.4, 132.8, 132.2, 129.8, 129.3, 127.1, 127.0, 126.5, 125.9, 124.1, 123.3, 103.5, 94.4, 80.8, 79.0, 70.6, 70.2, 60.1, 28.2, 28.1, 22.5, 21.4; MS (+CI) m/z (relative intensity) 359 (M+H+, 4), 269 (100); HRMS (+EI) calcd for C24H22O3 (M+) 358.1569, found 358.1574.

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-56dc7d357bf940f4be30b0a1b8e59c9c
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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