Isobutyl mercaptan → HCID 22103576, compound

HRID 1457193Notes

Reaction equation

HRID 1457193 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][SH:4].[H-].[Na+].Br[CH2:9][C:10]1[CH:15]=[C:14]([C:16]2[O:17][CH:18]=[CH:19][N:20]=2)[CH:13]=[CH:12][C:11]=1[C:21]1[C:22]([S:27]([N:30]([C:37]2[O:41][N:40]=[C:39]([CH3:42])[C:38]=2[CH3:43])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>CN(C=O)C.O>[CH3:42][C:39]1[C:38]([CH3:43])=[C:37]([N:30]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:27]([C:22]2[C:21]([C:11]3[CH:12]=[CH:13][C:14]([C:16]4[O:17][CH:18]=[CH:19][N:20]=4)=[CH:15][C:10]=3[CH2:9][S:4][CH2:3][CH:2]([CH3:5])[CH3:1])=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:29])=[O:28])[O:41][N:40]=1

Participants

6

Reactant 3

HCID 10558Isobutyl mercaptanHCID 24758Sodium hydrideHCID 10984709HCID 10984709, compound

Product 1

HCID 22103576HCID 22103576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5 equiv. of 2-methyl-1-propanethiol (125 mg, 1.39 mmol) in 1 ml of dry DMF was added 2.5 equiv. of 60% sodium hydride under an argon atmosphere at room temperature. The reaction mixture was stirred for 0.5 hrs. and then a solution of the title compound of Step (B) (160 mg, 0.278 mmol) in 1 ml of DMF was added. The reaction was stirred for 1 hr, diluted with 15 ml of water and extracted with ethyl acetate (3×20 ml). The ethyl acetate extract was washed with 5% lithium chloride (2×30 ml), brine and dried over sodium sulfate. The crude material was purified on a Merck silica column eluting with 40% ethyl acetate/hexane yielding 118 mg (68%) of the title compound of this step as a colorless oil.

Workup

  1. stirringThe reaction was stirred for 1 hr
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. extractionThe ethyl acetate extract
  4. washwas washed with 5% lithium chloride (2×30 ml), brine
  5. dry with materialdried over sodium sulfate
  6. customThe crude material was purified on a Merck silica column
  7. washeluting with 40% ethyl acetate/hexane yielding 118 mg (68%) of the title compound of this step as a colorless oil

Sources & evidence

ORD record
ord-c979a56315c545638a5ef9155e9eacb9
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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