Triethylamine → HCID 86699931, compound

HRID 530493Notes

Reaction equation

HRID 530493 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([OH:16])[CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[C:10](=[O:12])[O:16][C@H:13]1[CH2:14][CH3:15])([CH3:2])([CH3:3])[CH3:4].[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[C:10](=[O:12])[O:16][C@H:13]1[CH2:14][CH3:15])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724699PyBOPHCID 21091419HCID 21091419, compound

Product 2

HCID 86699930HCID 86699930, compoundYield 6%HCID 86699931HCID 86699931, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(tert-butoxycarbonylamino)-3-hydroxy-pentanoic acid (0.173 mg, 0.74 mmol) in dry CH2Cl2 (17 mL), Et3N (0.255 g, 2.3 mmol) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (0.463 mg, 0.89 mmol) were added at rt and the reaction stirred overnight. Solvent was evaporated and the crude product purified by typical silica gel column chromatography, eluting with petroleum ether/AcOEt (90:10) to give a mixture of diastereoisomers (anti:sin=8:2) (0.081 g) as a white solid. The diastereomeric mixture was further purified by typical silica gel column chromatography, eluting with petroleum ether/TBME (from 100:0 to 80:20) to give pure diastereoisomers, tert-butyl-N-[(2S*,3R*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamate (0.0095 g, 6%) and tert-butyl-N-[(2S*,3S*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamate (0.0382 g, 24%), as white solids.

Workup

  1. customSolvent was evaporated
  2. customthe crude product purified by typical silica gel column chromatography
  3. washeluting with petroleum ether/AcOEt (90:10)
  4. customto give
  5. additiona mixture of diastereoisomers (anti:sin=8:2) (0.081 g) as a white solid
  6. customThe diastereomeric mixture was further purified by typical silica gel column chromatography
  7. washeluting with petroleum ether/TBME (from 100:0 to 80:20)

Sources & evidence

ORD record
ord-e01e7df28841493d970bfb67edd4b237
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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