2-Propanethiol → HCID 21246126, compound

HRID 620422Notes

Reaction equation

HRID 620422 reaction equation
[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](Cl)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3].[CH:23]([SH:26])([CH3:25])[CH3:24].[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([S:26][CH:23]([CH3:25])[CH3:24])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 13319603HCID 13319603, compound

Product 1

HCID 21246126HCID 21246126, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzyl 6-(1-hydroxyethyl)-3-chloro-1-azabicyclo[3.2.0]hept-2-ene-7-one-2-carboxylate (32 mg) in anhydrous dimethylformamide (DMF, 2 ml) is cooled to -40° C. and stirred under a nitrogen atmosphere. A solution of isopropylmercaptan (8 mg) in anhydrous DMF (1 ml) containing 57% sodium hydride (4.4 mg) is added dropwise over 10 mins. The resulting solution is stirred for 2 hrs, with gradual warming to 0° C. The solution is diluted with ethyl acetate (20 ml), washed with water (5×10 ml) and brine, dried over MgSO4, filtered, and evaporated in vacuo. The residue is purified by plc on silica gel GF to yield benzyl 6-(1-hydroxyethyl)-3-isopropylthio-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. additionis added dropwise over 10 mins
  2. stirringThe resulting solution is stirred for 2 hrs
  3. washwashed with water (5×10 ml) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue is purified by plc on silica gel GF

Sources & evidence

ORD record
ord-a2a5214eee1a4bc1834859e9f5a1d29f
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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