Methanol → Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate

HRID 2264830Notes

Reaction equation

HRID 2264830 reaction equation
CC(OC([NH:8][C@@H:9]([CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:19][N:18]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)C.CO.C(Cl)(C)=O>C(OCC)(=O)C>[NH2:8][C@@H:9]([CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:19][N:18]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 59596689HCID 59596689, compound

Product 1

HCID 59596690Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoateYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate (D83, 0.439, 1.0 mmol), prepared by an analogous procedure to that described hereinabove, in ethyl acetate (4.5 ml) and methanol (0.5 ml) at 0° C. was added dropwise AcCl (0.5 ml, 7.0 mmol) and the mixture was stirred from 0° C. to r.t. for four hours. The solvent was removed under vacuum. The residue was diluted with a saturated solution of sodium bicarbonate and extracted with dichloromethane. The organic layer was dried, filtered and evaporated affording the title compound as yellow oil (0.30 g, 91%). Rt (HPLC): 3.60 min; MS: (ES/+) m/z: 329 [MH]+ C18H17FN2O3 requires 328; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.30-8.36 (m1H); 7.45-7.51 (m, 1H); 7.31-7.40 (m, 2H); 7.16-7.24 (m, 2H); 7.07-7.16 (m, 1H); 5.19 (s, 2H); 3.75-3.81 (m, 1H); 3.79 (s, 3H); 2.80-2.99 (m, 2H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residue was diluted with a saturated solution of sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-68a2396434ca469e8d4074285da4d576
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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