Butyric Acid → HCID 70035407, compound

HRID 411256Notes

Reaction equation

HRID 411256 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:19][C:20](=[N:51]O)[C:21]1[CH:49]=[CH:48][C:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]2[CH2:35][CH2:34][CH2:33][N:32]([C:36](=[O:47])[C@H:37]([NH:39][C:40]([C:42]3[O:43][CH:44]=[CH:45][CH:46]=3)=[O:41])[CH3:38])[CH2:31][CH2:30]2)=[CH:23][C:22]=1[F:50]>CN(C=O)C>[F:50][C:22]1[CH:23]=[C:24]([CH:48]=[CH:49][C:21]=1[C:20]1[N:51]=[C:1]([CH2:2][CH2:3][CH3:4])[O:6][N:19]=1)[O:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:35][CH2:34][CH2:33][N:32]([C:36](=[O:47])[C@H:37]([NH:39][C:40]([C:42]2[O:43][CH:44]=[CH:45][CH:46]=2)=[O:41])[CH3:38])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 682631,1'-Carbonyldiimidazole2×HCID 131723871HCID 131723871, compound

Product 1

HCID 70035407HCID 70035407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
115 °C

Procedure

Butyric acid (0.2 mmol) was treated with 0.5 mL of a 0.46 M solution (0.23 mmol) of 1,1′-carbonyldiimidazole (CDI) in DMF in a 4 mL vial. After mixing for 30 minutes, 0.75 mL of a 0.17 M solution of Example 141F (0.13 mmol) in DMF was added to the vial. The resulting solution was mixed for 4 hours at room temperature. A further 0.5 mL of 0.35 M solution of CDI (0.175 mmol) in DMF was added to the vial. The resulting mixture was heated at 115° C. for 6 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative HPLC to provide the desired products. 1H NMR (CDCl3) δ1.05 (t, 3H), 1.50 (m, 5H), 1.90 (m, 2H), 2.41 (m, 2H), 2.92 (t, 2H), 3.30-3.70 (m, 4H), 4.10-4.50 (m, 8H), 4.95 (m, 1H), 6.50 (m, 1H), 6.75 (m, 2H), 7.10 (m, 2H), 7.50 (m, 1H), 7.98 (m, 1H);

Workup

  1. additionAfter mixing for 30 minutes
  2. additionThe resulting solution was mixed for 4 hours at room temperature
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1019212f42d14582a15fcd6294c08232
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

Loading…