Water → HCID 57535901, compound

HRID 2358516Notes

Reaction equation

HRID 2358516 reaction equation
[Li+].[BH4-].CON(C)[C:6](=[O:41])[CH:7]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:19]=2)=[CH:13][C:12]=1[Cl:32].O.[CH2:44]1COCC1>C(O)C>[CH2:25]([O:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][CH2:8][CH:7]([NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH:6]([OH:41])[CH3:44])=[C:12]([Cl:32])[CH:13]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 23078159HCID 23078159, compound

Product 1

HCID 57535901HCID 57535901, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

LiBH4 (50 mg) was added to the compound of Example 130 in a mixture of THF (15 mL) and ethanol (3 mL). The mixture was stirred at room temperature for 1 hour. Following addition of water, the mixture was extracted with ethyl acetate and the extract was washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous sodium sulfate. The solvent was concentrated and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product as a colorless oil (320 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed sequentially with water
  3. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b117b0e64ac3448ebdbdb63e76fccf20
Source dataset
uspto-grants-2010_07
Patent number
US07763752B2

Reaction notes

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