Ethyl Acetate → HCID 86681595, compound

HRID 1912367Notes

Reaction equation

HRID 1912367 reaction equation
[NH2:1][C@H:2]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[CH2:33]([O:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCOC(C)=O>C1COCC1>[C:13]([O:12][C:11]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C@H:2]([NH:1][C:41](=[O:42])[O:40][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])=[CH:5][CH:6]=1)=[O:17])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86681594HCID 86681594, compound

Product 1

HCID 86681595HCID 86681595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of amine 62 (0.79 g, 2.43 mmol) in THF (20 mL) was added DiPEA (1.2 eq., 2.91 mmol, 482 μL), and benzylchloroformate (1.1 eq., 2.67 mmol, 392 μL) and the mixture was stirred for 4 hours in which a colorless solid precipitated. EtOAc was added and the mixture was extracted with 1 M aq. HCl (2×), sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (10%->75% EtOAc/PE) as a colorless foam (yield: 0.95 g, 2.06 mmol, 85%). 1H NMR (400 MHz, CDCl3): δ=7.33-7.23 (m, 7H), 7.14 (s, 1H), 7.05 (d, J=8.21 Hz, 2H), 5.80 (d, J=8.71 Hz, 1H), 5.04 (dd, J=26.77, 12.39 Hz, 2H), 4.98-4.94 (m, 1H), 3.62 (s, 3H), 3.13 (s, 3H), 3.01 (dd, J=13.65, 5.91 Hz, 1H), 2.85 (dd, J=13.58, 7.35 Hz, 1H), 1.49 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=171.72, 155.64, 152.64, 137.21, 136.07, 130.35, 129.52, 128.13, 127.69, 127.64, 118.18, 79.88, 66.41, 61.21, 51.95, 37.53, 31.73, 28.05 ppm. [α]D23=+8.1 (c=1, CHCl3). HRMS: calcd. for C24H31N3O6 458.22856 [M+H]+. found 458.22845.

Workup

  1. customprecipitated
  2. additionEtOAc was added
  3. extractionthe mixture was extracted with 1 M aq. HCl (2×), sat. aq. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0c19346e0c44d40867d921e967d3718
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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