tert-Butyl bromoacetate → HCID 69211810, compound

HRID 902919Notes

Reaction equation

HRID 902919 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])=[O:7].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[CH:4]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH:5]([C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1=[O:20])=[O:7])[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 69207787HCID 69207787, compound

Product 1

HCID 69211810HCID 69211810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of the compound of example 50 (2.40 g, 6.07 mmol) in anhydrous THF (60 mL) was cooled to −78° C. A solution of NaHDMS in THF (1M, 6.7 mmol, 6.7 mL) 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 (5 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 using ethyl acetate. The recombined organic layer was extracted successively with brine, saturated sodium hydrogen carbonate, brine and water. The solvent was evaporated following drying over sodium sulfate and filtration. The resultant crude material was flashed using 20% ethyl acetate in hexanes to give the product as a white solid. 1H-NMR(CDCl3, 300 MHz: 1.40, 1.41(2s, 9H); 1.74-1.92(m, 5H); 2.45-2.95(m, 4H); 3.31(m, 1H); 3.69, 3.73(2s, 3H); 4.11(m, 2H); 4.50, 4.66(2m, 1H); 7.25(m, 10H).

Workup

  1. stirringAfter stirring for 1 h at −78° C.
  2. custom3 h at −48° C., the reaction was quenched by the addition of a saturated ammonium chloride solution
  3. extractionThe mixture was extracted several times
  4. extractionThe recombined organic layer was extracted successively with brine, saturated sodium hydrogen carbonate, brine and water
  5. customThe solvent was evaporated
  6. dry with materialfollowing drying over sodium sulfate and filtration

Sources & evidence

ORD record
ord-a7cda27282fa4bf89cc810ed9a5d8b2b
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

Loading…