Sodium hydride → HCID 15035855, compound

HRID 1461472Notes

Reaction equation

HRID 1461472 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][S:11][CH2:12][CH:13]([OH:16])[CH2:14]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH:13]([OH:16])[CH2:12][S:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 15035854HCID 15035854, compound

Product 1

HCID 15035855HCID 15035855, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-(t-Butyloxycarbonyl-amino)-ethyl)-(3-chloro-2-hydroxypropyl)-thioether (30 g, 111.52 mmole) from Example 3, was dissolved in dimethylformamide (500 mL) at 0° C. and treated with sodium hydride (9.81 g, 245 mmole) in 3 portions over 15 minutes. The reaction was allowed to warm to room temperature over 1 hour and 15 minutes, poured into 2.5 L ice water and extracted with 3×1 L chloroform. The combined organic extracts were dried with brine and Na2SO4, evaporated, and the resulting residue chromatographed (3:1 hexane:ethyl acetate, silica gel) to obtain the product as a white solid (12.47 g, 48% yield) D.C.I.M.S. 234(M+H) M.P. 80°-82° C.

Workup

  1. extractionextracted with 3×1 L chloroform
  2. dry with materialThe combined organic extracts were dried with brine and Na2SO4
  3. customevaporated
  4. customthe resulting residue chromatographed (3:1 hexane:ethyl acetate, silica gel)

Sources & evidence

ORD record
ord-6a87ae30f51f4cd4880f179fc966cce0
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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