Hydrochloric Acid → HCID 58693684, compound

HRID 902779Notes

Reaction equation

HRID 902779 reaction equation
[CH3:1][C:2]1([CH3:31])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]3[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])=[CH:16][CH:15]=3)=[CH:11][C:5]=2[C:4](=[O:30])[O:3]1.CCN(C(C)C)C(C)C.[CH:41]1([CH2:46][CH2:47][C:48](Cl)=[O:49])[CH2:45][CH2:44][CH2:43][CH2:42]1.Cl>C(Cl)Cl>[CH:41]1([CH2:46][CH2:47][C:48]([N:12]([CH2:13][C:14]2[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[CH:16][CH:15]=2)[C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:31])([CH3:1])[O:3][C:4](=[O:30])[C:5]=3[CH:11]=2)=[O:49])[CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660393-Cyclopentylpropionyl chlorideHCID 81531DiisopropylethylamineHCID 11611418HCID 11611418, compound

Product 1

HCID 58693684HCID 58693684, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of benzyl 4-{[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}benzoate (430 mg) and DIEA (146 mg) in anhydrous DCM (5 nm) was added a solution of 3-cyclopentylpropanoyl chloride (182 mg, 1 M in DCM). The mixture was stirred 1 h at 0° C. then 3 h at rt. An aqueous solution of HCl (1N, 50 mL) was added and the resulting mixture was extracted with Et2O (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over MgSO4, filtered and evaporated under vacuum to give a light orange oil. Purification by chromatography (SiO2, DCM/c-Hex) gave the title compound as a colorless oil (499 mg, 89%). 1H NMR (CDCl3) δ 8.00 (d, J=8.3 Hz, 2H), 7.69 (d, J=2.3 Hz, 1H), 7.49-7.32 (m, 5H), 7.27 (d, J=7.5 Hz, 2H), 7.11-7.03 (m, 1H), 6.91 (d, J=8.6 Hz, 1H), 5.37 (s, 2H), 4.93 (s, 2H), 2.13-2.05 (m, 2H), 1.85 (s, 6H), 1.71-1.37 (m, 9H), 1.06-0.89 (m, 2H). M+(ESI): 542.3.

Workup

  1. custom3 h
  2. customat rt
  3. extractionthe resulting mixture was extracted with Et2O (3×50 mL)
  4. washThe combined organic layers were washed with brine (1×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customto give a light orange oil
  9. customPurification by chromatography (SiO2, DCM/c-Hex)

Sources & evidence

ORD record
ord-9c4f3adbe319436db1520f233dcab847
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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