1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 71138290, compound

HRID 1526409Notes

Reaction equation

HRID 1526409 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:26])[CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].CN(C)CCNC>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:15]([CH2:16][CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 79177tert-Butyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 11142747HCID 11142747, compound

Product 1

HCID 71138290HCID 71138290, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-benzyl-3-(4-(benzyloxy)butanoyl)oxazolidin-2-one (170 g, 482 mmol) in THF (1.0 L) at −78° C. was added LiHMDS (1.0 M in THF, 530 mL, 530 mmol) over 10 minutes via cannula. After stirring for 1 h at −78° C. tert-butyl bromoacetate (82.0 mL, 554 mmol) was added slowly over 45 min via syringe pump. The mixture was slowly allowed to warm to room temperature overnight. The reaction mixture was quenched with sat. ammonium chloride (300 mL) and stirred for 10 min, diluted further with H2O (500 mL), and extracted with MTBE (1.0 L). The organic layer was isolated, treated with N,N,N′-trimethylethylenediamine (5 mL) and shaken for 2 min in order to remove excess tert-butyl bromoacetate. The mixture was washed with 1 N HCl (2×750 mL), and brine (1.0 L). The organics were dried over MgSO4, filtered, and concentrated to give 262 g of crude (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-(benzyloxy)pentanoate.

Workup

  1. additionwas added slowly over 45 min via syringe pump
  2. customThe reaction mixture was quenched with sat. ammonium chloride (300 mL)
  3. additiondiluted further with H2O (500 mL)
  4. extractionextracted with MTBE (1.0 L)
  5. customThe organic layer was isolated
  6. stirringshaken for 2 min in order
  7. customto remove excess tert-butyl bromoacetate
  8. washThe mixture was washed with 1 N HCl (2×750 mL), and brine (1.0 L)
  9. dry with materialThe organics were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-84ca23100981453ab9e9b1e2e11862db
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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