Water → HCID 54022528, compound

HRID 370626Notes

Reaction equation

HRID 370626 reaction equation
[Cl:1][C:2]1[CH:17]=[C:6]([CH:7]=[N:8][C@H:9]([CH2:15][F:16])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:5]([OH:18])=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH:17]=1)[CH2:7][NH:8][C@H:9]([CH2:15][F:16])[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 136066983HCID 136066983, compound

Product 1

HCID 54022528HCID 54022528, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.42 g of 18 dissolved in a small amount of ethyl alcohol was added drop-by-drop to a mixture of 0.06 g of sodium borohydride, 3.6 ml of ethyl alcohol and 0.9 ml of water, at 10° C. The resulting solution was stirred and allowed to warm to room temperature overnight. The resulting mixture was quenched with water, and the resulting mixture was extracted with ethyl acetate. The extract was dried (Na2SO4), filtered and the solvent was evaporated to give 19, as an oily solid.

Workup

  1. customThe resulting mixture was quenched with water
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5c856e7de5f54e45b0c1fc6445eb596d
Source dataset
uspto-grants-1985_07
Patent number
US04528028

Reaction notes

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