Pyridine → HCID 9965205, compound

HRID 227146Notes

Reaction equation

HRID 227146 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:28]>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10]([F:28])=[O:11])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 9965205HCID 9965205, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (1.0 g, 3.77 mmol) in dichloromethane (18 mL) at −35° C. was added dry pyridine (320 μL, 3.96 mmol) and cyanuric fluoride (477 μL, 5.65 mmol) under an atmosphere nitrogen. The mixture was stirred for 1.5 hours while maintaining the temperature between −35 and −25° C. Ice was added to the reaction mixture and the mixture was stirred for 15 minutes. The organic layer was separated and the aqueous layer extracted with dichloromethane (2×10 mL). The combined organic extracts were washed with ice cold water (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give ((S)-1-fluorocarbonyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester which was used in the subsequent step without further purification.

Workup

  1. temperaturewhile maintaining the temperature between −35 and −25° C
  2. additionIce was added to the reaction mixture
  3. stirringthe mixture was stirred for 15 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×10 mL)
  6. washThe combined organic extracts were washed with ice cold water (15 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ac7b8d9057040d9bbcd499e511d167c
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

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