Propanethioamide → HCID 69055140, compound

HRID 1727227Notes

Reaction equation

HRID 1727227 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@:13]32[C@H:8]([C@H:9]([C:21](=O)[CH2:22]Br)[CH2:10][CH2:11][C@@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:25])(=[O:3])[CH3:2].[C:26]([NH2:30])(=[S:29])[CH2:27][CH3:28]>C(O)C>[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@@:13]32[C@H:8]([C@H:9]([C:21]2[N:30]=[C:26]([CH2:27][CH3:28])[S:29][CH:22]=2)[CH2:10][CH2:11][C@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2760628PropanethioamideHCID 86614065HCID 86614065, compound

Product 1

HCID 69055140HCID 69055140, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (3aS,4R,6aS,7R,10S,10aS)-7-(2-bromoacetyl)-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 164, 500 mg) in ethanol (5 ml) was added thiopropionamide (110 mg). The reaction mixture was stirred at room temperature for 24 hours and then partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic phase was dried (MgSO4), evaporated and purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (1:4) to give the product as a gum (345 mg).

Workup

  1. custompartitioned between saturated aqueous sodium chloride and ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. custompurified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-79861bddf2e84fa7b2c8005928a32695
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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