Hydrochloric Acid → HCID 69229713, compound

HRID 1181111Notes

Reaction equation

HRID 1181111 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH2:29][OH:30])([CH3:4])([CH3:3])[CH3:2].[CH:32]1([N:37]=[C:38]=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33]1.Cl.CCOCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH2:29][O:30][C:38](=[O:39])[NH:37][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 643500Cyclopentyl IsocyanateHCID 69231625HCID 69231625, compound

Product 1

HCID 69229713HCID 69229713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 15 mL round bottomed flask was charged with 3-{2-hydroxymethyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (0.10 g, 0.23 mmol), cyclopentylisocyanate (0.15 mL, 1.38 mmol), and anhydrous CH2Cl2 (0.75 mL). A 1.0 M HCl solution in ether (0.115 mL, 0.115 mmol) was added, and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 24 h. The reaction mixture was diluted with CH2Cl2, (30 mL), washed with brine, dried (Na2SO4), and concentrated to an oil. The crude product was purified using radial chromatography (EtOAc:hexanes 10:90 to 35:65) to a colorless oil (0.105 g, 83%). 1H NMR (400 MHz, CDCl3) 1.42 (s, 9H), 1.56-1.65 (m, 4H), 1.94-2.04 (m, 2H), 2.37 (s, 3H), 2.46 (t, J=7.6 Hz, 2H), 2.87 (t, J=8.1 Hz, 2H), 2.96 (t, J=6.6 Hz, 2H), 3.97 (br s, 1H), 4.22 (t, J=6.6 Hz, 2H), 4.76 (br s, 1H), 5.07 (s, 2H), 6.90 (dd, J=8.3, 2.4 Hz, 1H), 6.89 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 7.40-7.45 (m, 3H), 7.96-7.98 (m, 2H). MS (ES) m/e 549 (M+1).

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to an oil
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-fffe8bef1dc74390bdb1acade0d5d573
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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