Ethyl 3-isocyanatobenzoate → tert-butyl (2RS,4SR,5SR)-1-{2-[3-(3-(ethoxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylate

HRID 725874Notes

Reaction equation

HRID 725874 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:8]([C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:18])[CH2:7][CH:6]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:4].[N:32]([C:35]1[CH:36]=[C:37]([CH:43]=[CH:44][CH:45]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:33]=[O:34]>O1CCCC1>[CH2:41]([O:40][C:38]([C:37]1[CH:36]=[C:35]([NH:32][C:33](=[O:34])[NH:1][CH2:2][C:3]([N:5]2[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[CH:8]([C:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[O:18])[CH2:7][CH:6]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:4])[CH:45]=[CH:44][CH:43]=1)=[O:39])[CH3:42]

Participants

4

Reactant 2

HCID 589806Ethyl 3-isocyanatobenzoateHCID 86751934tert-butyl (2RS,4SR,5SR)-1-(2-aminoacetyl)-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylate

Product 1

HCID 86751933tert-butyl (2RS,4SR,5SR)-1-{2-[3-(3-(ethoxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

B tert-Butyl (2RS,4SR,5SR)-1-{2-[3-(3-(ethoxycarbomyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylate can be prepared as described in Example 17B, but from 1.7 g of tert-butyl (2RS,4SR,5SR)-1-(2-aminoacetyl)-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylate and 0.75 g of ethyl 3-isocyanatobenzoate in 80 cm3 of tetrahydrofuran. After treatment, there are obtained 1.5 g of tert-butyl (2RS,4SR,5SR)-1-{2-[3-(3-(ethoxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(morpholinocarbonyl)pyrrolidine-2-carboxylate in the form of a foam used as is in the subsequent syntheses.

Sources & evidence

ORD record
ord-08ecc0b5a86c4bbda91fab835a4de294
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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