Water → HCID 86753802, compound

HRID 1417608Notes

Reaction equation

HRID 1417608 reaction equation
[Si:1]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C:28](=[O:31])[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[Si:1]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C@H:28]([OH:31])[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86753803HCID 86753803, compound

Product 1

HCID 86753802HCID 86753802, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the above Compound (12b) (175 mg, 0.35 mmol) in 2 ml of methanol was added 17 mg (0.45 mmol) of sodium borohydride under ice-cooling, and the mixture stirred for 30 min. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (Merck, Lobar column, size A; chloroform:methanol=50:1) to give 106 mg (60%) of Compound (36).

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a column chromatography (Merck, Lobar column, size A

Sources & evidence

ORD record
ord-25175e702f284d1087d09a9a574403b8
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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