Acetic Acid → HCID 57808413, compound

HRID 2105176Notes

Reaction equation

HRID 2105176 reaction equation
N([O-])=O.[Na+].Cl.C(O)(=O)C.[CH:10]([C@@H:14]1[N:19]([CH3:20])[CH2:18][CH2:17][N:16]([C:21]([C:23]2[N:28]=[N:27][C:26]([C:29]([NH:31]N)=[O:30])=[C:25]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH:24]=2)=[O:22])[CH2:15]1)([CH2:12][CH3:13])[CH3:11].C(=O)(O)[O-].[Na+].N[C@H:43]([CH2:47][OH:48])[CH:44]([CH3:46])[CH3:45]>O>[OH:48][CH2:47][C@@H:43]([NH:31][C:29]([C:26]1[N:27]=[N:28][C:23]([C:21]([N:16]2[CH2:17][CH2:18][N:19]([CH3:20])[C@@H:14]([CH:10]([CH2:12][CH3:13])[CH3:11])[CH2:15]2)=[O:22])=[CH:24][C:25]=1[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH:44]([CH3:46])[CH3:45]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 640993L-ValinolHCID 23668193Sodium NitriteHCID 57808443HCID 57808443, compound

Product 1

HCID 57808413HCID 57808413, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 7 mL glass vial was charged with 500 μL water and cooled to 0° C. Sodium nitrite (1.8 mg, 0.026 mmol, 180 μL of 10 mg/mL aqueous solution), 1M hydrochloric acid (52 μL, 0.052 mmol) and acetic acid (0.039 mmol, 2.3 mg, 230 μL of 10 mg/mL aqueous solution) were added sequentially and stirred for ca. five minutes. A solution of acyl hydrazide 14 (5 mg in 500 μL THF:200 μL H2O, 0.013 mmol) was added slowly and the reaction mixture was stirred at 0° C. for 10 minutes. The acidic solution was neutralized with saturated sodium bicarbonate (2 mL) and extracted with cold diethyl ether (3×2 mL). The organic fractions were collected in a second 20 mL vial at 0° C., and 270 μL of a cold, ethereal solution of L-valinol (10 mg/mL, 0.026 mmol, 2.7 mg) was added slowly. The reaction was allowed to warm to room temperature, and stirred overnight. The solvent was evaporated, and the product was purified by silica gel chromatography (9.4:0.6:0.1% DCM:MeOH:Et3N, Rf=0.35) to give 5 mg (86% yield) of a colorless oil. MS: (ESI-TOF) MH+ expected: 448.3282, found: 448.3283.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 10 minutes
  2. extractionextracted with cold diethyl ether (3×2 mL)
  3. customThe organic fractions were collected in a second 20 mL vial at 0° C.
  4. temperatureto warm to room temperature
  5. stirringstirred overnight
  6. customThe solvent was evaporated
  7. customthe product was purified by silica gel chromatography (9.4:0.6:0.1% DCM:MeOH:Et3N, Rf=0.35)

Sources & evidence

ORD record
ord-36ada47f9b6f48d2b85235261ff52ddc
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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