tert-Butyl bromoacetate → HCID 69213128, compound

HRID 902930Notes

Reaction equation

HRID 902930 reaction equation
C(O[C:4](=O)[CH2:5][CH2:6][C:7]([N:9]1[CH:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][O:11][C:10]1=[O:21])=[O:8])C.BrC[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C1COCC1>[CH2:12]([O:11][C:10](=[O:21])[CH:6]([C:7]([N:9]1[CH:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][O:11][C:10]1=[O:21])=[O:8])[CH2:5][CH2:4][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:13]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 69211632HCID 69211632, compound

Product 1

HCID 69213128HCID 69213128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of the compound of example 67 (5.0 g, 16.38 mmol) in anhydrous THF (160 mL) was cooled to −78° C. A solution of NaHDMS in THF (1M, 16.4 mL, 16.4 mmol) was injected over 10 minutes. The reaction mixture was stirred for an additional 20 minutes, after which time, a solution of tert-butyl bromoacetate in anhydrous THF (10 mL) was slowly injected. After stirring for 1 h at −78° C. and 3 h at −48° C., the reaction was quenched by the addition of a saturated ammonium chloride solution. The mixture was extracted several times with ethyl acetate. The recombined organic layer was successively extracted with brine, a saturated sodium hydrogen carbonate solution, brine and water. The solvent was evaporated following drying over sodium sulfate and filtration. The resultant crude product was flashed with 20% ethyl acetate in hexanes to give the product as a white solid. 1H-NMR(CDCl3, 400 MHz: 1.24(t, J=7.2, 3H); 1.44(s, 9H); 2.54(m, 2H); 2.77(m, 3H); 3.31(m, 1H); 4.14(m, 4H); 4.43(m, 1H); 4.69(m, 1H); 7.26(m 5H).

Workup

  1. stirringAfter stirring for 1 h at −78° C. and 3 h at −48° C.
  2. customthe reaction was quenched by the addition of a saturated ammonium chloride solution
  3. extractionThe mixture was extracted several times with ethyl acetate
  4. extractionThe recombined organic layer was successively extracted with brine
  5. customThe solvent was evaporated
  6. dry with materialfollowing drying over sodium sulfate and filtration

Sources & evidence

ORD record
ord-3658b05d2a0d41c1a54e753d24c97a8f
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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