benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate → benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

HRID 1630258Notes

Reaction equation

HRID 1630258 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:3]1.[F:11][C:12]1[CH:43]=[CH:42][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C@H:26]3[NH:30][CH2:29][C@H:28]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:27]3)=[O:25])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1>>[NH:4]1[C:5]([CH2:7][C:8]([N:30]2[C@H:26]([C:24](=[O:25])[NH:23][C:20]3[CH:21]=[CH:22][C:17]([O:16][C:15]4[CH:14]=[CH:13][C:12]([F:11])=[CH:43][CH:42]=4)=[CH:18][CH:19]=3)[CH2:27][C@@H:28]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:29]2)=[O:10])=[CH:6][N:2]=[CH:3]1

Participants

3

Reactant 2

HCID 68201126benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamateHCID 178479752HCID 178479752, compound

Product 1

HCID 70641202benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamateYield 67%

Procedure

Proceeding as in Example 1, but substituting 4-imidazoleacetic acid hydrochloride and benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate gave Compound 253, benzyl (3R,5S)-1-(2-(1H-imidazol-5-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (1.01 g, 1.80 mmol, 67% yield). 1H-NMR (400 MHz, DMSO-d6): 11.92 (s, 1H), 10.06 (s, 1H), 7.92-7.42 (m, 4H), 7.40-7.28 (m, 5H), 7.23-7.17 (m, 2H), 7.06-6.94 (m, 5H), 5.02 (s, 2H), 4.50 (m, 1H), 4.28-4.13 (m, 1H), 3.85-3.41 (m, 4H), 2.38-2.02 (m, 2H). MS (EI) for C30H28FN5O5. found 557.9 (MH+).

Sources & evidence

ORD record
ord-1c9f8bfbba3d4ae7816113a52ccdf133
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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