Methanol → HCID 71621783, compound

HRID 871013Notes

Reaction equation

HRID 871013 reaction equation
[BH4-].[Na+].[NH2:3][C:4]([C:6]1[C:7]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[N:8][S:9][C:10]=1[NH:11][C:12]([NH:14][CH2:15][CH2:16][C:17](OC)=[O:18])=[O:13])=[O:5].CO>O1CCCC1>[OH:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]([NH:11][C:10]1[S:9][N:8]=[C:7]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:6]=1[C:4]([NH2:3])=[O:5])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 71621782HCID 71621782, compound

Product 1

HCID 71621783HCID 71621783, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (24.0 g 0.636 mol) was added to a solution of methyl 3-[({[4-(aminocarbonyl)-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]propanoate (25.0 g, 0.0636 mol) in tetrahydrofuran (1200 mL). The resulting suspension was heated to reflux. Methanol (200 mL) was added drop wise over 1 hr. and the reaction was refluxed for 1 hr. The reaction mixture was cooled to ambient temperature and solvent concentrated in vacuo. The residue taken in EtOAc (600 mL) and washed with water, 2 N HCl and brine then dried (sodium sulfate), filtered, solvent concentrated in vacuo to give the title compound as a yellow solid (18.8 g, 80%).

Workup

  1. temperatureThe resulting suspension was heated to reflux
  2. temperatureand the reaction was refluxed for 1 hr
  3. concentrationsolvent concentrated in vacuo
  4. washwashed with water, 2 N HCl and brine
  5. dry with materialthen dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationsolvent concentrated in vacuo

Sources & evidence

ORD record
ord-c88cf36e1ac545bb8700b1c1e0b19984
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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