2-Fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzoic Acid → 2-Fluoro-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612461Notes

Reaction equation

HRID 1612461 reaction equation
[CH2:1]([C@H:8]([NH:23]C(=O)C1C=CC(F)=C(Br)C=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])NCCC(C)(C)C)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:34][C:35]1[C:43]([N:44]2[CH2:48][CH2:47][CH2:46][C:45]2=[O:49])=[CH:42][C:41]([N:50]2[CH2:54][CH2:53][CH2:52][C:51]2=[O:55])=[CH:40][C:36]=1[C:37](O)=[O:38].N[C@H]([C@H]1OC(=O)[C@H](C)C1)CC1C=CC=CC=1>>[F:34][C:35]1[C:43]([N:44]2[CH2:48][CH2:47][CH2:46][C:45]2=[O:49])=[CH:42][C:41]([N:50]2[CH2:54][CH2:53][CH2:52][C:51]2=[O:55])=[CH:40][C:36]=1[C:37]([NH:23][C@H:8]([C@@H:9]1[CH2:10][C@@H:11]([CH3:12])[C:13](=[O:21])[O:22]1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:38]

Participants

4

Reactant 3

HCID 222530082-Fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzoic AcidHCID 68679802(3R,5S)-5-((S)-1-Amino-2-phenylethyl)-3-methyldihydrofuran-2-oneHCID 69589710N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-4-fluorobenzamide

Product 1

HCID 695896942-Fluoro-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D3 from 2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzoic acid (D40) and (3R,5S)-5-((S)-1-amino-2-phenylethyl)-3-methyldihydrofuran-2-one (D48).

Sources & evidence

ORD record
ord-7d61d87b7e7e4ebebce8783236b6d92e
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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