Ethyl bromoacetate → HCID 53774644, compound

HRID 322520Notes

Reaction equation

HRID 322520 reaction equation
[CH2:1]([C@H:8]1[NH:12][C:11](=[O:13])[C@@H:10]([CH2:14][CH2:15][C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CCOC(C)=O>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][N:12]1[C@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C@H:10]([CH2:14][CH2:15][C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[C:11]1=[O:13])[CH3:43]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18394801HCID 18394801, compound

Product 1

HCID 53774644HCID 53774644, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 12-3 (210 mg, 0.7257 mmol) and THF (5 mL) at −78° C. was added NaN(TMS)2 (0.943 mL, 0.943 mmol, 1.0 M in THF). After 30 min, ethyl bromoacetate (0.104 mL, 0.9434 mmol) was added and the reaction was warmed to 0° C. After 1.0 hour, the reaction mixture was diluted with EtOAc and then washed with sat NaHCO3, brine, dried (MgSO4), and concentrated to give 12-4 as a yellow oil.

Workup

  1. waitAfter 1.0 hour
  2. washwashed
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07d07bb2043c4ca69857eef5c6a033b5
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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