Sodium Methoxide → HCID 131736638, compound

HRID 1481315Notes

Reaction equation

HRID 1481315 reaction equation
[Br:1][C:2]1[N:3]([CH2:52][O:53][CH2:54][CH2:55][Si:56]([CH3:59])([CH3:58])[CH3:57])[C:4]2[C@@H:5]([N:27]([CH2:39][CH2:40][C:41]([C:43]3[C:48]([F:49])=[CH:47][CH:46]=[C:45]([Cl:50])[C:44]=3[F:51])=O)[C:28](=[O:38])[CH2:29]P(OCC)(OCC)=O)[CH2:6][CH2:7][CH2:8][C@@H:9]([CH3:26])[C:10](=[O:25])[NH:11][C:12]3[C:17]([C:18]=1[N:19]=2)=[CH:16][CH:15]=[C:14]([NH:20][C:21](=[O:24])[O:22][CH3:23])[CH:13]=3.C[O-].[Na+]>CO>[Br:1][C:2]1[N:3]([CH2:52][O:53][CH2:54][CH2:55][Si:56]([CH3:58])([CH3:57])[CH3:59])[C:4]2[C@@H:5]([N:27]3[C:28](=[O:38])[CH:29]=[C:41]([C:43]4[C:48]([F:49])=[CH:47][CH:46]=[C:45]([Cl:50])[C:44]=4[F:51])[CH2:40][CH2:39]3)[CH2:6][CH2:7][CH2:8][C@@H:9]([CH3:26])[C:10](=[O:25])[NH:11][C:12]3[C:17]([C:18]=1[N:19]=2)=[CH:16][CH:15]=[C:14]([NH:20][C:21](=[O:24])[O:22][CH3:23])[CH:13]=3

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131736636HCID 131736636, compound

Product 1

HCID 131736638HCID 131736638, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 227B (1.35 g, 1.27 mmol) in MeOH (36.3 ml) at 0° C. was added sodium methoxide (25% wt in MeOH) (1.454 ml, 6.36 mmol). The reaction was warmed to RT. After 1 h, the reaction mixture was concentrated. The residue dissolved in EtOAc, washed twice with 1.5 dipotassium phosphate solution (aq.), brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by normal phase column chromatography to give 227C (765 mg, 76%) as a tan solid. MS (ESI) m/z: 792/794 (M+H)+, bromine isotope.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue dissolved in EtOAc
  3. washwashed twice with 1.5 dipotassium phosphate solution (aq.), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by normal phase column chromatography

Sources & evidence

ORD record
ord-26980f5ca0cd437f98e0eef6a23120a6
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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