Triethylamine → HCID 59369836, compound

HRID 1662099Notes

Reaction equation

HRID 1662099 reaction equation
[NH2:1][CH2:2][C@H:3]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:7][C@@H:6]2[C@H:4]1[CH2:5]2.C(N(CC)CC)C.Cl[C:27]1[O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>CN(C)C=O.CCOC(C)=O>[O:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[NH:1][CH2:2][C@H:3]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:7][C@@H:6]2[C@H:4]1[CH2:5]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 59369849HCID 59369849, compound

Product 1

HCID 59369836HCID 59369836, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of racemic 7-3 (6.3 g, 25.6 mmol) in dimethylformamide (100 mL) at 25° C. was added triethylamine (3.88 g, 38.4 mmol) followed by 2-chlorobenzoxazole (5.11 g, 33.3 mmol) and the reaction mixture was stirred at ambient temperature for 24 h. The mixture was diluted with EtOAc (400 mL) and washed with water (4×100 mL). The combined organic layers were dried over MgSO4 and concentrated to an oil. The oil was purified by normal phase silica gel chromatography (0 to 100% EtOAc in hexanes) to afford the racemic product as an oil. ESI+ MS: [M+H]+ 364.3. This material was then separated into its respective enantiomers by the following method: ChiralPak AD 2×25 cm, 10 uM (40:60 hexane:EtOH, 0.1% diethylamine; flow rate=8 mL/min). Enantiomer A Rt=7.3 min; Enantiomer B Rt=8.7 min. 1H NMR (500 MHz, CDCl3) δ 7.43-7.42 (m, 2H), 7.36-7.33 (m, 4H), 7.08-7.02 (m, 3H), 4.64 (m, 1H), 4.52 (m, 1H), 4.43 (m, 2H), 3.42 (m, 1H), 3.29 (m, 1H), 3.14 (m, 1H), 2.71 (s, 3H), 1.84 (m, 1H), 1.60 (m, 1H), 1.43 (m, 1H), 0.560 (m, 1H). HRMS [M+H] C24H23F1N2O2S1 calc'd 423.1537, found 423.1542.

Workup

  1. washwashed with water (4×100 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated to an oil
  4. customThe oil was purified by normal phase silica gel chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4f0a46e72008417293d79c02ca3e542c
Source dataset
uspto-grants-2011_10
Patent number
US08030495B2

Reaction notes

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