Triethylamine → HCID 86751852, compound

HRID 613783Notes

Reaction equation

HRID 613783 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 1 N 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)δ3.33(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)δ40.4, 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 C26H25NO4: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 1 N 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-e2faae480d494135b434501d1214be66
Source dataset
uspto-grants-1999_12
Patent number
US06008386

Reaction notes

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