Triethylamine → HCID 86751852, compound

HRID 725245Notes

Reaction equation

HRID 725245 reaction equation
[CH:1]([NH:3][C@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:2].CCN([CH2:20][CH3:21])CC.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>CN(C)C1C=CN=CC=1.CS(C)=O.CCOC(C)=O>[CH2:1]([N:3]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@:4]([CH:20]=[CH2:21])([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22880942HCID 22880942, compound

Product 1

HCID 86751852HCID 86751852, compoundYield 166%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (±)-vinylphenylalanine (560 mg. 2.9 mmol), NEt3 (1.6 mL, 12 mmol) and 4-dimethylaminopyridine (71 mg, 0.59 mmol) in dry DMSO (3 mL) at 10° C. was added benzyl chloroformate (1.9 mL, 13 mmol), dropwise and with stirring. After being stirred for 1.5 h at 50° C., the reaction mixture was diluted with EtOAc (150 mL) and extracted with NaHCO3 (aq, 50 mL). The organic layer was further extracted with 1N HCl (50 mL) and brine (50 mL). After drying (MgSO4), the volatiles were evaporated in vacuo and the residue purified by flash SiO2 chromatography (10% Et2O-hexane) to give 19 (1.0 g, 82%) as a white solid: mp 68°-70° C.; 1H NMR (500 MHz, CDCl3) δ 3.33 (d, J=13 Hz, 1 H); 3.62 (d, J=13 Hz, 1 H); 5.10-5.25 (m, 4 H); 5.27 (d, J=10 Hz, 1 H); 5.28 (d, J=17 Hz, 1 H); 5.68 (s, 1 H); 6.08 (dd, J=10, 17 Hz, 1 H); 6.90-6.91 (m, 2 H); 7.10-7.20 (m, 3 H); 7.26-7.43 (m, 10 H); 13C NMR (125 MHz, CDCl3) δ 40.4, 65.1, 66.5, 67.8, 116.2, 126.9, 128.1, 128.20, 128.23, 128.4, 128.5, 128.6, 130.0, 130.3, 135.0, 135.4, 136.6, 136.8, 154.4, 171.2; IR (film)3420-3330, 1723 cm-1 ; HRMS (FAB, 3-NOBA) calcd for C26H25NO4Na (M+Na)+ 438.1681, obsd 438.1685. Anal. Calcd for C26H25 NO4 : C, 75.16; H, 6.07; N, 3.37. Found: C, 74.98; H, 6.22; N, 3.37.

Workup

  1. stirringAfter being stirred for 1.5 h at 50° C.
  2. extractionextracted with NaHCO3 (aq, 50 mL)
  3. extractionThe organic layer was further extracted with 1N HCl (50 mL) and brine (50 mL)
  4. dry with materialAfter drying (MgSO4)
  5. customthe volatiles were evaporated in vacuo
  6. customthe residue purified by flash SiO2 chromatography (10% Et2O-hexane)

Sources & evidence

ORD record
ord-fae1781169b14047a8c54f0479f53891
Source dataset
uspto-grants-1998_01
Patent number
US05705660

Reaction notes

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