Chlorotrimethylsilane → HCID 59263856, compound

HRID 644985Notes

Reaction equation

HRID 644985 reaction equation
[CH:1]1([NH:8][CH2:9][CH:10]([N:12]([CH2:23][CH2:24][C:25]2[C:33]3[S:32][C:31](=[O:34])[NH:30][C:29]=3[C:28]([OH:35])=[CH:27][CH:26]=2)[C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C[Si](Cl)(C)C.[C:48](Cl)(=[O:51])[CH:49]=[CH2:50]>C(Cl)Cl>[C:48]([N:8]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]([N:12]([CH2:23][CH2:24][C:25]1[C:33]2[S:32][C:31](=[O:34])[NH:30][C:29]=2[C:28]([OH:35])=[CH:27][CH:26]=1)[C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:11])(=[O:51])[CH:49]=[CH2:50]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 59263959HCID 59263959, compound

Product 1

HCID 59263856HCID 59263856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Benzyl [2-(cycloheptylamino)-1-methylethyl][2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]carbamate (0.46 g) in CH2Cl2 (10 mL) was added triethylamine (0.773 mL) and trimethylsilyl chloride (0.586 mL) and the mixture was stirred for 1 h at room temperature. The reaction mixture was cooled in ice and acryloyl chloride (0.0976 mL) was added. The mixture was allowed to warm slowly to RT, diluted with CH2Cl2 and washed with 2M HCl and brine. Drying and evaporation afforded an orange foam (470 mg), which was used directly in the next step.

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. temperatureto warm slowly to RT
  3. washwashed with 2M HCl and brine
  4. customDrying
  5. customevaporation

Sources & evidence

ORD record
ord-71b1bf211db7460c8b2d454dd835aa21
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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