Pyridine → HCID 10625297, compound

HRID 2185936Notes

Reaction equation

HRID 2185936 reaction equation
[C:1]([NH:11][C@H:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].N1C=CC=CC=1.[F:34][C:35]([F:41])([F:40])[S:36](Cl)(=[O:38])=[O:37].CCOC(C)=O>C(Cl)Cl>[C:1]([NH:11][C@H:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][S:36]([C:35]([F:41])([F:40])[F:34])(=[O:38])=[O:37])=[CH:18][CH:19]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 79000Trifluoromethanesulfonyl chlorideHCID 11428694Z-Tyr-OtBu

Product 1

HCID 10625297HCID 10625297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.15 g (4.1 mmol) N-(CBZ)-(L)-tyrosine, tert-butyl ester in 150 mL of dry methylene chloride at 0° C. was added 12.9 g (164 mmol) of pyridine followed by the dropwise addition of 12.68 g (4.5 mmol) of trifluoromethylsulfonyl chloride. The reaction mixture was stirred at room temperature for 4 hours at which time TLC (25% EtOAc in hexanes) indicated complete consumption of starting material. The reaction mixture was shaken with 1N HCl (3×100 mL), saturated NaHCO3 solution (2×50 mL), and brine (1×50 mL). The organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give N-(CBZ)-4-(trifluoromethylsulfonyloxy)-(L)-phenylalanine, tert-butyl ester.

Workup

  1. customconsumption of starting material
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65def68cc85b443381ac3b64b2cb79cc
Source dataset
uspto-grants-2002_06
Patent number
US06403584B1

Reaction notes

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