Hydrochloric Acid → HCID 68297366, compound

HRID 919944Notes

Reaction equation

HRID 919944 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[C:6]=1[CH2:19][N:20]([CH2:31][C:32]([O:34][CH3:35])=[O:33])S(C1C=CC(C)=CC=1)(=O)=O)=O.C[O-].[Na+].Cl>CO.[Cl-].[Na+].O>[CH3:35][O:34][C:32]([C:31]1[C:3]([OH:2])=[C:5]2[C:6](=[CH:19][N:20]=1)[N:7]([CH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)[C:8](=[O:12])[C:9]([Br:11])=[CH:10]2)=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86714156HCID 86714156, compound

Product 1

HCID 68297366HCID 68297366, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-Bromo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1-thiazol-2-ylmethyl-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (41 mg, 0.070 mmol) was dissolved in 5 mL of MeOH. NaOMe solution (0.050 mL, 0.21 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, followed by addition of brine (10 mL), and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-3% MeOH/CH2Cl2) to give 28.6 mg of the title compound. MS: (+) m/z 396.07, 398.03 (M+1, 79/81Br).

Workup

  1. extractionthe resulting mixture 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 (0-3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5d4a8edc37d34c83aa7cc6e86fd16b32
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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