Ethyl 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate → 5-(3-(4-(Tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

HRID 2067657Notes

Reaction equation

HRID 2067657 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(OCC)=O.[C:27]([O:31][C:32]([NH:34][C:35]1[CH:58]=[CH:57][C:38]([CH2:39][N:40]2[CH2:44][CH2:43][N:42]([C:45]3[S:49][C:48]([C:50]([O:52]CC)=[O:51])=[C:47]([CH3:55])[CH:46]=3)[C:41]2=[O:56])=[CH:37][CH:36]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32]([NH:34][C:35]1[CH:58]=[CH:57][C:38]([CH2:39][N:40]2[CH2:44][CH2:43][N:42]([C:45]3[S:49][C:48]([C:50]([OH:52])=[O:51])=[C:47]([CH3:55])[CH:46]=3)[C:41]2=[O:56])=[CH:37][CH:36]=1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 58031549Ethyl 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateHCID 58031558Ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 580316425-(3-(4-(Tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidYield 64%

Procedure

Following the procedure as described in Example 54, making variations as required to replace ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)-thiophene-2-carboxylate with ethyl 5-(3-(4-(tert-butoxycarbonylamino)benzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate, the title compound was obtained as a pinkish solid in 64% yield: 1H NMR (300 MHz, DMSO-d6) δ 9.35 (br s, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.17 (d, J=8.4 Hz, 2H), 6.27 (s, 1H), 4.31 (s, 2H), 3.85-3.76 (m, 2H), 3.45-3.36 (m, 2H), 2.39 (s, 3H), 1.46 (s, 9H); MS (ES−) m/z 430.4 (M−1).

Sources & evidence

ORD record
ord-b1b94d950d5d4b98a471c56662888b93
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…