alpha-(R)-(3-(S)-((4-(benzothiazol-2-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester → alpha-(R)-(3-(S)-((4-(Benzothiazol-2-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic Acid

HRID 1068144Notes

Reaction equation

HRID 1068144 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][N:19]([C@H:28]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:29]([O:31]CC3C=CC(OC)=CC=3)=[O:30])[CH2:18]2)[CH2:12][CH2:11]1>C(O)=O>[NH4+:3].[OH-:30].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][N:19]([C@H:28]([CH:41]3[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]3)[C:29]([OH:31])=[O:30])[CH2:18]2)[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 57100094alpha-(R)-(3-(S)-((4-(benzothiazol-2-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester

Product 2

HCID 14923Ammonium HydroxideHCID 20664158alpha-(R)-(3-(S)-((4-(Benzothiazol-2-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic AcidYield 167.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 50 mg of α-(R)-(3-(S)-((4-(benzothiazol-2-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester (from Step C) in 2 mL of formic acid (96%) was stirred at room temperature for 18 hours. After concentration under reduced pressure, the residue was purified by flash chromatography eluting with 10% MeOH in CH2Cl2, and then CHCl3: MeOH: NH4OH=80:15:1 to give 34 mg of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ1.10-2.35 (m, 9H), 2.41 (br d, 2H), 2.56 (br t, 2H), 2.8-3.25 (m, 10 H), 3.4-3.75 (m, 6H), 7.25-7.45 (m, 6H), 7.48 (t, J=7.3 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.93 (d, J=8.2 Hz, 1H); ESI-MS 518 (M+1); HPLC A: 2.88 min.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by flash chromatography
  3. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-d01c562c92ff49ed8fd2f19fd63608b7
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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