Hydrochloric Acid → HCID 68297664, compound

HRID 919971Notes

Reaction equation

HRID 919971 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[C:6]=1[CH2:21][N:22]([CH2:33][C:34]([O:36][CH3:37])=[O:35])S(C1C=CC(C)=CC=1)(=O)=O)=O.C[O-].[Na+].Cl>CO>[CH3:37][O:36][C:34]([C:33]1[C:3]([OH:2])=[C:5]2[C:6](=[CH:21][N:22]=1)[N:7]([C@@H:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14])[C:8](=[O:12])[C:9]([Br:11])=[CH:10]2)=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 68297558HCID 68297558, compound

Product 1

HCID 68297664HCID 68297664, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-5-Bromo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1-(1-phenyl-ethyl)-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (3.5 g, 5.92 mmol) was dissolved in 120 mL of MeOH and placed in ice bath. NaOMe solution (4.1 mL, 17.8 mmol, 4.375 M in MeOH) was added and the mixture was stirred for 16 h at r.t. 1 M HCl was added to acidify the mixture, and the resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (30-100% CH2Cl2/hexanes) to give 2.13 g of the title compound as a yellow solid. MS: (−) m/z 401.18, 403.19 (M−1, 79/81Br).

Workup

  1. extractionthe resulting suspension was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (30-100% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-ff39e58ca73544818c93c9fd26bef697
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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