Dichloromethane → HCID 58746441, compound

HRID 724721Notes

Reaction equation

HRID 724721 reaction equation
[C:1]([OH:4])(=O)C.[NH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C@@H:14]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]2)=[C:18]([CH3:30])[CH:17]=1.[CH3:42][Si:43]([CH3:50])([CH3:49])[CH2:44][CH2:45][O:46][CH2:47]Cl.C(N([CH2:58][CH3:59])C(C)C)(C)C.C(Cl)Cl>Cl>[O:28]=[S:26]1(=[O:27])[CH:22]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][C@H:14]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:6]3[N:5]([CH2:47][O:46][CH2:45][CH2:44][Si:43]([CH3:50])([CH3:49])[CH3:42])[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]=3)=[CH:17][C:18]=2[CH3:30])[CH2:23][C:24](=[O:29])[N:25]1[CH2:1][O:4][CH2:58][CH2:59][Si:43]([CH3:49])([CH3:44])[CH3:42]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86602083HCID 86602083, compound

Product 1

HCID 58746441HCID 58746441, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of benzyl (1S)-1-(1H-benzimidazol-2-yl)-2-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-methylphenyl]ethylcarbamate acetate (956 mg, 1.65 mmol), [β-(trimethylsilyl)ethoxy]methyl chloride (731 μL, 4.13 mmol), N,N-diisopropylethylamine (1.73 mL, 9.91 mmol) and methylene chloride (30.0 mL) was stirred at 25° C. for 3 h. The reaction was diluted with 1 N HCl solution and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (0.82 g, 64%). 1H NMR (400 MHz, CD3OD): δ 7.79 (m, 1H), 7.68 (m, 1H), 7.4 (m, 8H), 7.11 (s, 1H), 5.5 (m, 4H), 5.1 (m, 4H), 3.75 (m, 2H), 3.55 (m, 2H), 3.3 (m, 4H), 2.52 (s, 1.5H), 2.40 (s, 1.5H), 1.02 (m, 2H), 0.94 (m, 2H), 0.11 (s, 9H), 0.01 (s, 9H); MF=C39H54N32O7SSi2; LCMS found for C39H55N4O7SSi2 (M+H)+: m/z=779.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d563e55c059e4823a2a07394966cf429
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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