Ammonia → HCID 58380833, compound

HRID 1948144Notes

Reaction equation

HRID 1948144 reaction equation
N.[Na].C([O:10][CH:11]1[CH2:16][CH2:15][C:14]([CH:19]([NH2:22])[CH2:20][CH3:21])([O:17][CH3:18])[CH2:13][CH2:12]1)C1C=CC=CC=1>O1CCCC1>[NH2:22][CH:19]([C:14]1([O:17][CH3:18])[CH2:15][CH2:16][CH:11]([OH:10])[CH2:12][CH2:13]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 58380816HCID 58380816, compound

Product 1

HCID 58380833HCID 58380833, compoundYield 160.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35 mL of ammonia were condensed into a Schlenk flask, cooled in a dryice-isopropanol bath. 170 mg of sodium were dissolved and 1.1 g of 40, dissolved in 3 mL of dry tetrahydrofurane, were added. After complete conversion, the reaction was quenched by addition of methanol and the mixture was warmed to room temperature. The solvents were evaporated and the crude material was taken up in methanol and dilute hydrochloric acid and evaporated several times to give 1.19 g of crude product as a cis/trans mixture, which was used directly in the next step, Rt=0.10 min (Method P). Detected mass: 188.1 (M+H+).

Workup

  1. customcondensed into a Schlenk flask
  2. temperaturecooled in a dryice-isopropanol bath
  3. additionwere added
  4. customAfter complete conversion, the reaction was quenched by addition of methanol
  5. customThe solvents were evaporated
  6. customdilute hydrochloric acid and evaporated several times

Sources & evidence

ORD record
ord-8d4e74ef477547958d14174f3bba178a
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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