Water → HCID 54366438, compound

HRID 1708332Notes

Reaction equation

HRID 1708332 reaction equation
O=[C:2]1[CH2:21][NH:20][CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[NH:13][CH2:12][C:11](=O)[NH:10][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.O>O1CCCC1>[CH:9]12[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[NH:3][CH2:2][CH2:21][NH:20][CH:19]1[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]1)[NH:13][CH2:12][CH2:11][NH:10]2

Participants

4

Reactant 2

HCID 962WaterHCID 53848153HCID 53848153, compound

Product 1

HCID 54366438HCID 54366438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of BH3 in tetrahydrofuran (265 ml.) was slowly added to 10.2 g. (33.1 mmol.) of compound (A). The solution was boiled for 24 hours. Water was then added dropwise to destroy the excess BH3 and the reaction mixture was brought to dryness. The solid residue was added to 265 ml. of a 6M hydrochloric acid solution and the mixture was refluxed overnight. Hydrochloric acid was eliminated under vacuum. The residue was digested in ethanol, filtered and dissolved in water. Concentrated ammonia was added until the pH became strongly basic. The inorganic precipitate that formed was filtered off and the filtrate was extracted with methylene chloride yielding 6.3 g. of compound (B) as a white solid after elimination of the solvent.

Workup

  1. customto destroy the excess BH3 and the reaction mixture
  2. additionThe solid residue was added to 265 ml
  3. temperatureof a 6M hydrochloric acid solution and the mixture was refluxed overnight
  4. filtrationfiltered
  5. dissolutiondissolved in water
  6. additionConcentrated ammonia was added until the pH
  7. customThe inorganic precipitate that formed
  8. filtrationwas filtered off
  9. extractionthe filtrate was extracted with methylene chloride yielding 6.3 g

Sources & evidence

ORD record
ord-4150957ccd5545c98e5601e8f4a7fe41
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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