1-Ethyl-3,3-bis(phenylmethyl)-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone → N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-4,4-bis(phenylmethyl)prolinamide

HRID 554157Notes

Reaction equation

HRID 554157 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10]C(=O)[C@@H]1CC(C)(C)C(=O)N1CC.[CH2:23]([N:25]1[C:32](=[O:33])[C:31]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])[CH3:24].C(N1C(=O)C(C)(C)C[C@H]1C(O)=O)C.[CH2:61]([N:63]1[CH:67]([CH2:68][O:69][C:70]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:66][C:65]([CH2:96]C2C=CC=CC=2)([CH2:89]C2C=CC=CC=2)[C:64]1=[O:103])[CH3:62]>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:27](=[O:29])[C@@H:26]1[CH2:30][C:31]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:32](=[O:33])[N:25]1[CH2:23][CH3:24].[CH2:23]([N:25]1[C:32](=[O:33])[C:31]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])[CH3:24].[CH2:61]([N:63]1[CH:67]([CH2:68][O:69][C:70]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=2)[C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:66][C:65]([CH3:96])([CH3:89])[C:64]1=[O:103])[CH3:62]

Participants

7

Reactant 4

HCID 674588911-Ethyl-3,3-bis(phenylmethyl)-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinoneHCID 674606891-Ethyl-5-oxo-4,4-bis(phenylmethyl)prolineHCID 674615891-Ethyl-4,4-dimethyl-5-oxoprolineHCID 67461683N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-4,4-dimethyl-5-oxoprolinamide

Product 3

HCID 67458898N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-4,4-bis(phenylmethyl)prolinamideHCID 674593161-Ethyl-3,3-dimethyl-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinoneHCID 674606891-Ethyl-5-oxo-4,4-bis(phenylmethyl)proline

Procedure

N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-4,4-bis(phenylmethyl)prolinamide was prepared in a manner analogous to that described above for the synthesis of N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-4,4-dimethyl-5-oxoprolinamide (E130) but using 1-ethyl-5-oxo-4,4-bis(phenylmethyl)proline in the place of 1-ethyl-4,4-dimethyl-5-oxoproline. 1-Ethyl-5-oxo-4,4-bis(phenylmethyl)proline was prepared in a manner analogous to that described for 1-ethyl-4,4-dimethyl-5-oxoproline in example 130 above but using 1-ethyl-3,3-bis(phenylmethyl)-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone (isolated as a side-product in method B, Example 37) in place of 1-ethyl-3,3-dimethyl-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone.

Sources & evidence

ORD record
ord-aefefb8ee98a4e9389328bc1f465581c
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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