Water → HCID 25195716, compound

HRID 1876314Notes

Reaction equation

HRID 1876314 reaction equation
C[O:2][C:3](=O)[CH2:4][C@@H:5]1[CH2:9][S:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:14][C:13]=3[NH:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[N:6]1.O1CCCC1.[BH4-].[Li+].O>O1CCCC1>[CH:25]1([NH:24][C:13]2[CH:14]=[C:15]([CH2:19][S:20]([CH3:23])(=[O:21])=[O:22])[CH:16]=[C:17]3[C:12]=2[NH:11][C:10]([C:7]2[S:8][CH2:9][C@@H:5]([CH2:4][CH2:3][OH:2])[N:6]=2)=[CH:18]3)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 25195714HCID 25195714, compoundHCID 131718764lithium borohydride THF

Product 1

HCID 25195716HCID 25195716, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (720 mg, 1.60 mmol) prepared in Example 68 was dissolved in tetrahydrofuran (20 ml). 2 M lithium borohydride tetrahydrofuran solution (1.6 ml, 3.2 mmol) was added thereto, and the mixture was stirred for 3 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and separated by column chromatography to give the title compound (292 mg, Yield 43%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under reduced pressure
  7. customseparated by column chromatography

Sources & evidence

ORD record
ord-baa89ac953524c5a86ecacf0b7d82964
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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