Phosphoric Acid → Tert-butyl ((2S,3S)-1-(benzyloxy)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate

HRID 527381Notes

Reaction equation

HRID 527381 reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([CH2:14][O:15][Si](C)(C)C(C)(C)C)[N:3]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.F.N1C=CC=CC=1.P(=O)(O)(O)O>C1COCC1.N1C=CC=CC=1>[OH:15][CH2:14][C@H:4]1[N:3]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:2](=[O:1])[C@H:5]1[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 64774Pyridine, hydrofluoride (1:1)HCID 67121282n-{(3s,4s)-2-Oxo-1-(phenylmethoxy)-4-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]azetidin-3-yl}(tert-butoxy)carboxamide

Product 1

HCID 13488997Tert-butyl ((2S,3S)-1-(benzyloxy)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamateYield 98.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-{(3S,4S)-2-oxo-1-(phenylmethoxy)-4-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]azetidin-3-yl}(tert-butoxy)carboxamide (2.80 g, 6.41 mmol) was dissolved in THF (50 mL) and pyridine (5 mL). Pyridine-hydrofluoride complex (4.0 mL, 2.6 eq of pyridine, 24 eq of HF) was added at −20° C. After 10 min, the mixture was warmed up at room temperature and stirred for 3.5 h. Phosphoric acid buffer (0.025 M, KH2PO4/Na2HPO4; ratio 1/1, 400 mL) was added and the resulting solution was extracted with ethyl acetate (3×100 mL). The organic phase was dried over Na2SO4 and the solvent was evaporated in vacuo. 2.04 g of the desired product was obtained and used for the next step.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (3×100 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0ecc21c1f0b6413581a26f29ecfeaae1
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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