Sodium hydride → HCID 70981039, compound

HRID 1475429Notes

Reaction equation

HRID 1475429 reaction equation
[H-].[Na+].C(OC([N:10]1[CH2:15][C@@H:14]([CH3:16])[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C@@H:11]1[CH:24]([OH:30])[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)=O)(C)(C)C.[Cl-].[NH4+]>C1COCC1>[C:20]([O:19][C:17]([N:13]1[CH2:12][C@H:11]([CH:24]([OH:30])[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[NH:10][CH2:15][C@H:14]1[CH3:16])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70980091HCID 70980091, compound

Product 1

HCID 70981039HCID 70981039, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (60% in mineral oil, 0.08 g, 1.9 mmol) was added to (2R,5R)-2-(hydroxy-thiazol-2-yl-methyl)-5-methyl-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.393 g, 0.95 mmol) in THF (4.8 mL) at 0° C. (ice bath) under nitrogen. The reaction was heated to 70° C. for 18 h. The reaction was cooled to room temperature and saturated aqueous ammonium chloride was added and the mixture extracted with EtOAc (3×). The combined organic extracts were dried with sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60) gave the title compound (0.111 g) MS: [M+H]+=314.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionthe mixture extracted with EtOAc (3×)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washChromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-e4d78312f85d425580aa3e67b3ab04d0
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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