Sodium borohydride → HCID 178483912, compound

HRID 1063625Notes

Reaction equation

HRID 1063625 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][CH2:8][N:9]([CH3:36])[C:10](=[O:35])[CH2:11][CH2:12][O:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([N:20]([CH3:34])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:16][CH2:15]1)C.C1COCC1.CO>O>[OH:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:36])[C:10](=[O:35])[CH2:11][CH2:12][O:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([N:20]([CH3:34])[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)(=[O:22])=[O:23])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuranHCID 178472031HCID 178472031, compound

Product 1

HCID 178483912HCID 178483912, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

181 mg (4.78 mmol, 10 eq) of NaBH4 were added portionwise to a solution of 250 mg (0.48 mmol) of trans-3-[methyl-(3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionyl)-amino]-propionic acid ethyl ester in 6 mL of a mixture of THF:MeOH (1:1) at 0° C. The reaction mixture was stirred at RT for 4 h. Water was added and the reaction was extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography with a gradient of CH2Cl2:MeOH 98:2 to 95:5 to yield 55 mg (24%) of trans-N-(3-hydroxy-propyl)-N-methyl-3-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionamide as colorless oil, MS: 481(MH+).

Workup

  1. extractionthe reaction was extracted with CH2Cl2
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by flash chromatography with a gradient of CH2Cl2:MeOH 98:2 to 95:5

Sources & evidence

ORD record
ord-98303c01bbb64eb78436dda48967fa62
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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