Sodium Methoxide → HCID 86585064, compound

HRID 1264410Notes

Reaction equation

HRID 1264410 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:12](=[O:39])[CH2:13][NH:14][C:15]([C@@H:17]2[CH2:21][C@@H:20]([S:22]C(=O)C)[CH2:19][N:18]2[S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])=[O:16])[CH3:11])=[CH:6][CH:5]=1.[CH3:41][O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:5]=[CH:6][C:7]([N:10]([C:12](=[O:39])[CH2:13][N:14]([C:15]([C@@H:17]2[CH2:21][C@@H:20]([SH:22])[CH2:19][N:18]2[S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])=[O:16])[CH3:41])[CH3:11])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86585062HCID 86585062, compound

Product 1

HCID 86585064HCID 86585064, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

80 mg (0.134 mmol) (2S,4R)-4-[[[[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester in 5 ml methanol were treated with 335 μl 0.6M (0.2 mmol) sodium methanolate in methanol at 0° C. for 1 h. The solution was poured on EtOAc/1M KHSO4 and the inorganic phase was extracted with EtOAc, the organic phases were washed with brine, dried over Na2SO4 and were evaporated. Column chromatography with EtOAc yielded 70 mg (quant) (2S,4R)-4-[[[[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester as white foam, MS: 556 (MH+).

Workup

  1. additionThe solution was poured on EtOAc/1M KHSO4
  2. extractionthe inorganic phase was extracted with EtOAc
  3. washthe organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. customwere evaporated

Sources & evidence

ORD record
ord-0583595e19b2496fb5d312d72562ce05
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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