Triethylamine → HCID 67251544, compound

HRID 79335Notes

Reaction equation

HRID 79335 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22])[C@@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 14037016186132-80-9

Product 1

HCID 67251544HCID 67251544, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2R,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (4.812 g, 20.81 mmol) in DMF (30 mL) at 0° C. was added tert-butylchlorodimethylsilane (9.409 g, 62.43 mmol) and triethylamine (10.53 g, 104.0 mmol). The cold bath was removed and the reaction mixture was stirred for 16 hours. The mixture was diluted with EtOAc (50 mL) and 10% NaOH (30 mL), and the phases were separated. The organic phase was washed with 10% NaOH. The combined aqueous phases were acidified with concentrated HCl until pH=2. The aqueous phase was extracted with DCM. The combined organic phases were dried (Na2SO4) and concentrated under reduced pressure to give the crude product 6.86 g).

Workup

  1. customThe cold bath was removed
  2. additionThe mixture was diluted with EtOAc (50 mL) and 10% NaOH (30 mL)
  3. customthe phases were separated
  4. washThe organic phase was washed with 10% NaOH
  5. extractionThe aqueous phase was extracted with DCM
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00728ebb150446b7bb9c807f555dcd91
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…