Water → methyl (1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-aminophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate

HRID 410459Notes

Reaction equation

HRID 410459 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:15]2[S:19][C:18]([C@@:20]3([OH:32])[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH3:29])=[O:27])[C:22]([CH3:31])([CH3:30])[CH2:21]3)=[N:17][CH:16]=2)[CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)(=[O:3])[CH3:2].O.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C.[Fe]>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:15]2[S:19][C:18]([C@@:20]3([OH:32])[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH3:29])=[O:27])[C:22]([CH3:31])([CH3:30])[CH2:21]3)=[N:17][CH:16]=2)[CH:9]=[C:10]([NH2:12])[CH:11]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67433015methyl (1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-nitrophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate

Product 1

HCID 58456151methyl (1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-aminophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the product of Step 5 (200 mg, 0.43 mmol) dissolved in ethanol (3.7 mL) and water (0.57 mL) was added iron (72.4 mg, 1.29 mmol). Saturated aqueous ammonium chloride (0.57 mL) was added and heated the mixture to 70° C. The reaction was stirred for 8 h at 70° C., then cooled to room temperature, diluted with ethyl acetate, and filtered. The filter cake was washed with 1:1 ethanol:ethyl acetate, and then the filtrate was washed with 1:1 water:saturated aqueous sodium bicarbonate. The filtrate was extracted with ethyl acetate (3×) and the combined organic layers were washed with brine, and then dried over sodium sulfate, filtered, and concentrated to give methyl (1S,4R)-4-(5-{3-[(acetyloxy)methyl]-5-aminophenyl}-1,3-thiazol-2-yl)-4-hydroxy-2,2-dimethylcyclohexanecarboxylate (186.5 mg, 0.43 mmol, 100% yield) as a yellow foam. MS ESI: [M+H]+ m/z 433.2.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filter cake was washed with 1:1 ethanol
  4. washethyl acetate, and then the filtrate was washed with 1:1 water
  5. extractionThe filtrate was extracted with ethyl acetate (3×)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ae0e6c4cd3874a75bd227a09aed9b245
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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