Tetrahydrofuran → HCID 11257778, compound

HRID 1611972Notes

Reaction equation

HRID 1611972 reaction equation
C1COCC1.C([O:8][C:9](=O)[C:10]([C:13]1[CH:14]=[N:15][C:16]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=3)=[O:24])=[C:17]([O:19][CH2:20][CH3:21])[CH:18]=1)([OH:12])[CH3:11])C.[BH4-].[Li+]>[Cl-].[Na+].O>[OH:12][C:10]([C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH3:21])[C:16]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=3)=[O:24])=[N:15][CH:14]=1)([CH3:11])[CH2:9][OH:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 11350945HCID 11350945, compound

Product 1

HCID 11257778HCID 11257778, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a THF (2 mL) solution of 2-{6-[(5-chloro-1H-indole-2-carbonyl)-amino]-5-ethoxy-pyridin-3-yl}-2-hydroxy-propionic acid ethyl ester (90 mg) was added lithium borohydride (2M in THF), and the reaction was stirred for 1 hr. The reaction mixture was diluted with brine and extracted with EtOAc. The extracts were dried over magnesium sulfate, filtered, and evaporated to yield a colorless syrup. Further purification on a silica gel prep plate (10% methanol/methylene chloride) afforded 21 mg of the pure title compound as an off-white solid. LC/MS+=390.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a colorless syrup
  6. customFurther purification on a silica gel prep plate (10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-da4803a3d8be4acf9d453efa406518d6
Source dataset
uspto-grants-2006_01
Patent number
US06992092B2

Reaction notes

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