Water → HCID 18958572, compound

HRID 1708334Notes

Reaction equation

HRID 1708334 reaction equation
O=[C:2]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]([CH2:18][CH2:19][OH:20])[CH2:12][C:11](=O)[NH:10][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3]1.B.C1COCC1.O>O1CCCC1>[OH:20][CH2:19][CH2:18][N:13]1[CH2:12][CH2:11][NH:10][CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:3][CH2:2][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuran2×HCID 18958566HCID 18958566, compound

Product 1

HCID 18958572HCID 18958572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a dry flask under nitrogen was placed 3.00 g. (10 mmol.) of compound (A) and 100 ml. of a 1M solution of BH3.THF in anhydrous tetrahydrofuran. The reaction mixture was refluxed for 12 hours. Water was added dropwise until no reaction was taking place with the excess of BH3.THF. The solvent was stripped off on a rotary evaporator after addition of a few ml. of methanol to avoid excessive foaming. The solid residue was treated with about 10 ml. of a concentrated solution of LiOF.H2O until the pH reached 12-13. This aqueous phase was extracted 6 times with 100 ml. of methylene chloride. The extracts were collected and dried over magnesium sulfate. The solvent was removed under vacuum to yield 2.62 g. of Compound (B) as a white powder that was used in the next step without further purification.

Workup

  1. customInto a dry flask under nitrogen was placed
  2. temperatureThe reaction mixture was refluxed for 12 hours
  3. customThe solvent was stripped off on a rotary evaporator
  4. additionafter addition of a few ml
  5. additionThe solid residue was treated with about 10 ml
  6. extractionThis aqueous phase was extracted 6 times with 100 ml
  7. customThe extracts were collected
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed under vacuum
  10. customto yield 2.62 g
  11. customof Compound (B) as a white powder that was used in the next step without further purification

Sources & evidence

ORD record
ord-ec955a9d493d4325bf58f4e3d6c11482
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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