Lithium Hydroxide → HCID 86638099, compound

HRID 907363Notes

Reaction equation

HRID 907363 reaction equation
[CH2:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=2)=[O:13])=[N:8][C:7]=1[C:23]([O:25]C)=[O:24])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH-].[Li+]>O.CO>[CH2:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:22])[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=2)=[O:13])=[N:8][C:7]=1[C:23]([OH:25])=[O:24])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86638100HCID 86638100, compound

Product 1

HCID 86638099HCID 86638099, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-isopentyl-2-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1,3-thiazole-4-carboxylate (660 mg, 1.74 mmol; see step (iii) above) was suspended in a mixture of water (25 mL) and methanol (5 mL) containing lithium hydroxide (125 mg, 5.21 mmol). The reaction mixture was stirred vigorously for 48 h at room temperature. Some of the methanol was removed under partial reduced pressure at 50° C. The cooled solution was extracted with ether and the ethereal layer was discarded. The aqueous layer was cooled to 0° C. and acidified by adding HCl (Concentrated) dropwise with stirring. The pale yellow solid was filtered off, washed with water and dried overnight at 45° C. under reduced pressure to give the sub-title compound (584 mg, 92% yield), m.p.=296-300° C.

Workup

  1. customSome of the methanol was removed under partial reduced pressure at 50° C
  2. extractionThe cooled solution was extracted with ether
  3. temperatureThe aqueous layer was cooled to 0° C.
  4. additionby adding HCl (Concentrated) dropwise
  5. stirringwith stirring
  6. filtrationThe pale yellow solid was filtered off
  7. washwashed with water
  8. customdried overnight at 45° C. under reduced pressure

Sources & evidence

ORD record
ord-7b31888372024b14b7836a3a3521a7e7
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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