Benzyl rel-({(3r,4r)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate → Rel-({(3s,4s)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetic acid

HRID 564396Notes

Reaction equation

HRID 564396 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][C@@H:18]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[C@H:17]([O:37][CH2:38][C:39]([O:41]CC4C=CC=CC=4)=[O:40])[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1>CO>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:19][C@H:18]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[C@@H:17]([O:37][CH2:38][C:39]([OH:41])=[O:40])[CH2:16]3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 67004369Benzyl rel-({(3r,4r)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate

Product 1

HCID 57813981Rel-({(3s,4s)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl rel-({(3R,4R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetate in methanol (400 μL) was added and Palladium (10%) on Carbon (50 mg) the was purged with hydrogen gas for two minutes; the reaction was then subjected to 1 atmosphere of hydrogen gas for two hours. The flask was purged with argon; the mixture was filtered, then purified by preparative HPLC to afford rel-({(3S,4S)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetic acid. 1H-NMR (CDCl3) δ: 1.10-1.25 (m, 2H), 1.80-2.40 (m, 4H), 2.50-2.70 (m, 2H), 2.95-3.15 (m, 1H), 3.20-3.35 (m, 1H), 3.40-3.80 (m, 4H), 3.85 (s, 3H), 3.90-4.40 (m, 5H), 4.40-60 (m, 2H), 6.62 (t, J=7.8 Hz, 1H), 7.10-7.15 (m, 1H), 7.38-7.58 (m, 1H), 7.60 (m, 2H), 8.00-8.25 (m, 2H), 9.45 (bs, 1H). MS m/z: 581 (M+1).

Workup

  1. customPalladium (10%) on Carbon (50 mg) the was purged with hydrogen gas for two minutes
  2. customThe flask was purged with argon
  3. filtrationthe mixture was filtered
  4. custompurified by preparative HPLC
  5. customto afford rel-({(3S,4S)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]-4-[({[3-trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-3-yl}oxy)acetic acid

Sources & evidence

ORD record
ord-c261d9e4d799463bba1a1102752f40d3
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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