Triethylamine → HCID 59436371, compound

HRID 1961398Notes

Reaction equation

HRID 1961398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11](O)[CH2:10][C@@:9]1([CH3:17])[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.CCN(CC)CC>>[CH3:17][C@@:9]12[CH2:10][C@@H:11]([CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[O:15][C:14]2=[O:16]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 59436402HCID 59436402, compound

Product 1

HCID 59436371HCID 59436371, compoundYield 49%

Procedure

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid (860 mg, 3.51 mmol) and diphenyl phosphorazidate (700 mg, 2.54 mmol) (DPPA) was added Et3N (0.680 mL, 4.88 mmol) at 0° C. The reaction mixture was stirred at RT for 6 h, quenched with water, extracted with EtOAc (3×40 ml). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by Biotage (0-30% EtOAc/hex, 1.2 L) to give 101C (235 mg, 49%). 1H NMR (CDCl3, 400 MHz) δ 4.87 (1H, d, J=1.01 Hz), 3.53-3.62 (m, 1H), 3.44-3.53 (m, 1H), 1.98-2.10 (m, 2H), 1.74 (s, 3H), 1.40 (s, 9H); 13C NMR (CDCl3, 101 MHz) δ 172.45 (1C), 154.93 (1C), 81.22 (1C), 75.03 (1C), 64.02 (1C), 53.16 (1C), 46.35 (1C), 28.26 (1C), and 13.96 (3C).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc (3×40 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Biotage (0-30% EtOAc/hex, 1.2 L)

Sources & evidence

ORD record
ord-cbfc1a47b5c942419aff33d319f6a6b6
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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