Sodium borohydride → HCID 22315087, compound

HRID 966592Notes

Reaction equation

HRID 966592 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:28])[CH:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[S:9][CH:10]=1)=O)C.[BH4-].[Na+]>O1CCCC1>[CH:15]1([CH2:14][CH:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([CH2:4][OH:3])[N:7]=2)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 46221596HCID 46221596, compound

Product 1

HCID 22315087HCID 22315087, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-4-carboxylic acid ethyl ester (prepared as in Example 1(B)(f), 200 mg, 0.45 mmol) in tetrahydrofuran (3 mL) at 25° C. was slowly treated with sodium borohydride (26.0 mg, 0.68 mmol). The reaction mixture was heated under reflux for 48 h. The reaction mixture was allowed to cool to 25° C. and then slowly quenched by the dropwise addition of water. The resulting reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-(4-hydroxymethyl-thiazol-2-yl)-propionamide (44.9 mg, 25%) as a white solid: mp 88-90° C.; EI-HRMS m/e calcd for C18H20Cl2N2O2S (M+) 398.0623, found 398.0631.

Workup

  1. customat 25° C.
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 48 h
  4. customslowly quenched by the dropwise addition of water
  5. customThe resulting reaction mixture
  6. customwas partitioned between water and ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9873689f199f480494a68fa3835c431c
Source dataset
uspto-grants-2005_10
Patent number
US06951945B2

Reaction notes

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