2-(3-Aminophenyl)ethan-1-ol → Cyclopentyl N-[2-(3-{6-amino-5-[(4-fluorophenyl)carbonyl]-2-oxopyridin-1(2H)-yl}phenyl)ethyl]-L-leucinate

HRID 1667384Notes

Reaction equation

HRID 1667384 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11](CCOS(C)(=O)=O)=[CH:10][CH:9]=2)[C:6](=[O:21])[CH:5]=[CH:4][C:3]=1[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1.N[C:32]1C=C(C=C[CH:40]=1)CCO.[CH:41]1([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH2:49])[CH2:45][CH2:44][CH2:43][CH2:42]1>>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[C:12]([CH2:32][CH2:40][NH:49][C@H:48]([C:47]([O:46][CH:41]3[CH2:42][CH2:43][CH2:44][CH2:45]3)=[O:54])[CH2:50][CH:51]([CH3:52])[CH3:53])[CH:11]=[CH:10][CH:9]=2)[C:6](=[O:21])[CH:5]=[CH:4][C:3]=1[C:22]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:30]

Participants

4

Reactant 3

HCID 149389872-(3-Aminophenyl)ethan-1-olHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate2×HCID 58608538Methanesulfonic acid 2-{4-[6-amino-5-(4-fluoro-benzoyl)-2-oxo-2H-pyridin-1-yl]-phenyl}-ethyl ester

Product 1

HCID 57658334Cyclopentyl N-[2-(3-{6-amino-5-[(4-fluorophenyl)carbonyl]-2-oxopyridin-1(2H)-yl}phenyl)ethyl]-L-leucinate

Procedure

Example 70 was synthesised using similar methodology to Intermediate 4J (instead using 3-aminophenethyl alcohol) and L-Leucine cyclopentyl ester (Intermediate 8).

Workup

  1. customExample 70 was synthesised

Sources & evidence

ORD record
ord-734c844e101f480aa573bb3fe8d82c39
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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