Acetone → HCID 86663349, compound

HRID 1012328Notes

Reaction equation

HRID 1012328 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23](C)(C)[CH3:24])[C:17](=[S:19])[NH2:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](OC(OCC)CBr)[CH3:29].[CH3:37][C:38](C)=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][CH2:23][CH2:24][CH2:37][CH3:38])[C:17]2[S:19][CH:28]=[CH:29][N:18]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 58826571HCID 58826571, compound

Product 1

HCID 86663349HCID 86663349, compoundYield 42%

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl (S)-[2-(4-benzyloxyphenyl)-1-thiocarbamoylethyl]carbamate (250 mg, 0.647 mmol) in acetone (5 ml) was added bromoacetaldehyde diethyl acetal (149 μl, 0.970 mmol), and the mixture was stirred at 65° C. for 14 hr. The mixture was further heated to 75° C. and stirred for 5 hr. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give text-butyl (S)-[2-(4-benzyloxyphenyl)-1-(thiazol-2-yl)ethyl]carbamate (112 mg, yield 42%).

Workup

  1. temperatureThe mixture was further heated to 75° C.
  2. stirringstirred for 5 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ae207682a1df419f8cc8650f156e4cb7
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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