Dimethylformamide → HCID 11518406, compound

HRID 1790100Notes

Reaction equation

HRID 1790100 reaction equation
O[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=[N:3]1.[CH:11]([N:14]([CH:17]([CH3:19])[CH3:18])[CH2:15][CH3:16])([CH3:13])C.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]C(O)=O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:53][N:54]([CH:56]=[O:57])C>>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][C:56]([NH:54][C:53]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:5]=2[CH:10]=[N:3][N:2]3[CH2:16][CH2:15][N:14]2[CH2:11][CH2:13][CH2:19][C@H:17]2[CH3:18])=[O:57])=[CH:32][CH:33]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 81531Diisopropylethylamine

Product 1

HCID 11518406HCID 11518406, compound

Conditions

Temperature
55 °C

Procedure

The residue, 46.0 mg N-hydroxybenzotriazole (0.341 mmol), 0.170 mL of diisopropylethylamine (0.976 mmol), and 65.0 mg (0.269 mmol) of (4-benzyloxy-phenyl)-acetic acid was dissolved in 4 mL of DMF followed by the addition of 0.520 mg of PS-DCC resin (1.3 mmol/g, 0.676 mmol, 2.83 equiv) after which it was shaken and heated to 55° C. for 12 hours. The mixture was cooled to room temperature and the contents filtered through a sintered glass funnel. The filtrate was concentrated under reduced pressure and the residue prurified by silica gel column chromatography eluting with 50–100% ethyl acetate (3.5% triethylamine) to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 0.88 (d, J=6.10 Hz, 3 H), 1.20 (m, 1 H), 1.59 (m, 2 H), 1.80 (m, 1 H), 2.11 (q, J=8.81 Hz, 1 H), 2.30 (m, 1 H), 2.46 (m, 1 H), 3.06 (m, 1 H), 3.20 (m, 1 H), 3.71 (s, 2 H), 4.44 (t, J=6.78 Hz, 2 H), 5.09 (s, 2 H), 6.98 (m, 2 H), 7.36 (m, 9 H), 7.63 (m, 1 H), 8.26 (s, 1 H), 10.11 (s, 1 H); MS (DCI/NH3) m/z 469 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe contents filtered through a sintered glass funnel
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washeluting with 50–100% ethyl acetate (3.5% triethylamine)

Sources & evidence

ORD record
ord-fe535716bd464677bd0d45fbe39c8032
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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