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

HRID 725869Notes

Reaction equation

HRID 725869 reaction equation
CC1(C)CC(C2C=CC=CC=2)N([C:13](=[O:30])[CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:20]=2)=[O:17])C1(C(N1CCCCC1)=O)C([O-])=O.[CH3:43][C:44]1([CH3:66])[CH2:49][CH2:48][CH2:47][N:46]([C:50]([CH:52]2[CH:56]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[NH:55][CH:54]([C:63]([O-:65])=[O:64])[CH2:53]2)=[O:51])[CH2:45]1.N(C1[CH:71]=[C:72]([CH:78]=CC=1)[C:73](OCC)=O)=C=O>O1CCCC1>[CH3:43][C:44]1([CH3:66])[CH2:49][CH2:48][CH2:47][N:46]([C:50]([CH:52]2[CH:56]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[N:55]([C:13](=[O:30])[CH2:14][NH:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:20]=3)=[O:17])[CH:54]([C:63]([O:65][C:72]([CH3:78])([CH3:73])[CH3:71])=[O:64])[CH2:53]2)=[O:51])[CH2:45]1

Participants

5

Reactant 3

HCID 589806Ethyl 3-isocyanatobenzoateHCID 86751923HCID 86751923, compoundHCID 867519254-(3,3-Dimethylpiperidinocarbonyl)-5-phenylpyrrolidine-2-carboxylate

Product 1

HCID 86751922tert-butyl (2RS,4SR,5SR)-4-(3,3-dimethylpiperidinocarbonyl)-1-{2-[3-(3-(ethoxycarbonyl)phenyl]ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

B tert-Butyl (2RS,4SR,5SR)-4-(3,3-dimethylpiperidinocarbonyl-1-{2-[3-(3-(ethoxycarbonyl)phenyl]ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate can be prepared as described in Example 17B, but from 2.7 g of tert-butyl (2RS,4SR,5SR)-1-(2-aminoacetyl)-4-(4-(3,3-dimethylpiperidinocarbonyl)-5-phenylpyrrolidine-2-carboxylate and 1.17 g of ethyl 3-isocyanatobenzoate in 120 cm3 of tetrahydrofuran. After treatment, there are obtained 2.3 g of tert-butyl (2RS,4SR,5SR)-4-(3,3-dimethylpiperidinocarbonyl)-1-{2-[3-(3-(ethoxycarbonyl)phenyl]ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate in the form of a foam used as is in the subsequent syntheses.

Sources & evidence

ORD record
ord-e96a76d4b6a142899e7779292c97dfd5
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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