Water → HCID 57918176, compound

HRID 1961627Notes

Reaction equation

HRID 1961627 reaction equation
[BH4-].[Na+].O.[CH2:4]([O:6][C:7]([C@@H:9]1[CH2:11][C@H:10]1[CH:12]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])S(C1C=CC(C)=CC=1)(=O)=O)=[O:8])[CH3:5]>O1CCCC1>[CH2:4]([O:6][C:7]([C@@H:9]1[CH2:11][C@H:10]1[CH2:12][NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[O:8])[CH3:5]

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydride2×HCID 66627665HCID 66627665, compound

Product 1

HCID 57918176HCID 57918176, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium Borohydride (2.3 g, 58.55 mol) was suspended in tetrahydrofuran (150 mL) and 4 mL of water was added. (13.3 g, 33.46 mmol) of trans-2-[tert-Butoxycarbonylamino-(toluene-4-sulfonyl)-methyl]-cyclopropanecarboxylic acid ethyl ester was added portionwise (0.8 g portions) and the temperature was kept to 18-30° C. After 1.5 h water (4 mL) and 0.4 g (10.15 mmol) of sodium borohydride were added again. The resulting mixture was quenched with ammonium chloride 2M (300 mL) and 100 mL of 1M K2CO3 and stirring was continued for 0.5 h. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (300 mL) and the combined organic layers were dried over MgSO4 and concentrated to dryness under vacuum and purified with column chromatography on silica with heptane/AcOEt (9/1) to obtain 7.5 g (92.1% yield) of the title compound. as a white solid. MS (m/e): 244.1 (M+H+)

Workup

  1. customwas kept to 18-30° C
  2. customThe resulting mixture was quenched with ammonium chloride 2M (300 mL) and 100 mL of 1M K2CO3
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (300 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated to dryness under vacuum
  7. custompurified with column chromatography on silica with heptane/AcOEt (9/1)

Sources & evidence

ORD record
ord-f052792e6081407d8091adb33b086d95
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

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