Lithium diisopropylamide → HCID 178455195, compound

HRID 46127

Reaction equation

HRID 46127 reaction equation
C12CC(CC1)C[C@@H]2NC1SC(CC2CCN(C(OC(C)(C)C)=O)CC2)(C)C(=O)N=1.[CH:30]12[CH2:36][CH:33]([CH2:34][CH2:35]1)[CH2:32][CH:31]2[NH:37][C:38]1[S:39][CH:40]([CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[C:41](=[O:43])[N:42]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:63][CH2:64][O:65][Si:66]([C:69]([CH3:72])([CH3:71])[CH3:70])([CH3:68])[CH3:67]>>[CH:30]12[CH2:36][CH:33]([CH2:34][CH2:35]1)[CH2:32][CH:31]2[NH:37][C:38]1[S:39][C:40]([CH2:63][CH2:64][O:65][Si:66]([C:69]([CH3:72])([CH3:71])[CH3:70])([CH3:68])[CH3:67])([CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[C:41](=[O:43])[N:42]=1

Participants

5

Reactant 4

HCID 2724682Lithium diisopropylamideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178451850tert-butyl 4-[[2-[[(2S)-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylateHCID 1784552022-(2-bicyclo[2.2.1]heptanylamino)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1,3-thiazol-4-one

Product 1

HCID 178455195HCID 178455195, compound

Procedure

The title compound was prepared according to the procedure described in the preparation of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate by using 2-(bicyclo[2.2.1]heptan-2-ylamino)-5-(2-(tert-butyldimethylsilyloxy)ethyl)thiazol-4(5H)-one (630 mg, 1.71 mmol), lithium diisopropylamide (Aldrich, 2.0 M in heptane/THF/ethylbenzene, 4.27 mL, 8.55 mmol), and (2-bromoethoxy)(tert-butyl)dimethylsilane (Aldrich, 2.46 g, 10.25 mmol). The title compound was obtained as a sticky orange solid (771 mg). MS (ESI, pos. ion) m/z: 413 (M-TBDMS+2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6b5df5eb90b243ed9d0d8c270c613a6b
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Linked notes

Loading…