Pyridine → HCID 66856160, compound

HRID 2037451Notes

Reaction equation

HRID 2037451 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([N:30]2[CH2:35][CH2:34][C@@:33]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)([CH2:36][CH2:37][OH:38])[O:32][C:31]2=[O:46])[CH3:29])=[CH:24][CH:23]=1.N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:38][CH2:37][CH2:36][C@@:33]1([C:39]2[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=2)[O:32][C:31](=[O:46])[N:30]([C@H:28]([C:25]2[CH:26]=[CH:27][C:22]([C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[F:14])=[CH:23][CH:24]=2)[CH3:29])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 53361128HCID 53361128, compound

Product 1

HCID 66856160HCID 66856160, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-nitrophenyl chloroformate (133 mg, 0.66 mmol) in dichloromethane (1 mL) was added to a solution of (S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (100 mg, 0.22 mmol) and pyridine (608 mg, 7.7 mmol) in dichloromethane (2.8 mL). The mixture was stirred at it overnight. The reaction was quenched with 1 N HCl (7 mL), and the mixture was extracted with EtOAc (3×10 mL). The combined organic layer was washed with brine, dried and concentrated to give 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl 4-nitrophenyl carbonate (70 mg, crude), which was used for the next step without purification.

Workup

  1. customThe reaction was quenched with 1 N HCl (7 mL)
  2. extractionthe mixture was extracted with EtOAc (3×10 mL)
  3. washThe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9430b3e2fb5d46e7b739470abeb1c7b8
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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