(2-Bromoethoxy)-tert-butyldimethylsilane → Ethyl 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 2067650Notes

Reaction equation

HRID 2067650 reaction equation
BrCCO[Si](C(C)(C)C)(C)C.Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:15]=1.[CH3:28][C:29]1[CH:33]=[C:32]([N:34]2[CH2:38][CH2:37][NH:36][C:35]2=[O:39])[S:31][C:30]=1[C:40]([O:42][CH2:43][CH3:44])=[O:41]>>[C:23]([O:22][C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:36]2[CH2:37][CH2:38][N:34]([C:32]3[S:31][C:30]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:29]([CH3:28])[CH:33]=3)[C:35]2=[O:39])=[CH:15][CH:16]=1)=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 46835249tert-Butyl [4-(chloromethyl)phenyl]carbamateHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031549Ethyl 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateYield 80%

Procedure

Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).

Sources & evidence

ORD record
ord-200e8bbf6c6b4eba9c12c4e3ec5524f9
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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