Dichloromethane → HCID 89668617, compound

HRID 1482246Notes

Reaction equation

HRID 1482246 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:10](=[O:17])[N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[C:26]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])[CH2:27][CH2:28][CH2:29][C:30]#[CH:31].C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C.CCCCCC.C(OCC)(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:21]([O:20][C:19]([NH:18][C@H:9]([C:10](=[O:17])[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][C:26]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:3][CH:4]=1)=[O:25])([CH3:24])([CH3:23])[CH3:22]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 109649121,1-Dimethylethyl 5-hexynoateHCID 89668441HCID 89668441, compound

Product 1

HCID 89668617HCID 89668617, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

tert-Butyl (S)-(3-(4-iodophenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl)carbamate (Compound SP413, Boc-Phe(4-I)-pip) (6.00 g, 13.09 mmol), tert-butyl hex-5-ynoate (Compound SP423) (4.40 g, 26.2 mmol) and triethylamine (5.47 ml, 39.3 mmol) were dissolved in DMF (60.0 ml), CuI (0.125 g, 0.655 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.538 g, 0.655 mmol) were added and the mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with hexane/ethyl acetate (1/1) and washed with a saturated aqueous ammonium chloride solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-60:40) to afford the title compound SP425 (6.19 g, 95%).

Workup

  1. washwashed with a saturated aqueous ammonium chloride solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-60:40)

Sources & evidence

ORD record
ord-9916b4137b7347798b261124a2b51c70
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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