Toluene → Ammonium Hydroxide

HRID 1068183Notes

Reaction equation

HRID 1068183 reaction equation
C[O:2]C1C=CC(C[O:8][C:9](=[O:49])[C@H:10]([N:17]2[CH2:21][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@H:19]([CH2:28][N:29]3[CH2:34][CH2:33][CH:32]([N:35]4[C:39](=[O:40])[C:38]([CH2:41][C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)=[C:37]([CH3:48])[NH:36]4)[CH2:31][CH2:30]3)[CH2:18]2)[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=CC=1.C1(C)C=CC=CC=1>C(O)=O>[OH-:2].[NH4+:17].[CH2:41]([C:38]1[C:39](=[O:40])[N:35]([CH:32]2[CH2:31][CH2:30][N:29]([CH2:28][C@@H:19]3[C@@H:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:21][N:17]([C@H:10]([CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[C:9]([OH:49])=[O:8])[CH2:18]3)[CH2:34][CH2:33]2)[NH:36][C:37]=1[CH3:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 70124577alpha-(R)-(3-(S)-((4-(4-benzyl-5-methyl-1H-pyrazol-3(2H)-on-2-yl)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 2

HCID 14923Ammonium HydroxideHCID 20664139alpha-(R)-(3-(S)-((4-(4-benzyl-5-methyl-1H-pyrazol-3(2H)-on-2-yl)-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The material from Step C was dissolved in ˜2 ml of 96% formic acid and stirred at room temperature for 3 hours. Toluene (10 mL) was then added and the mixture concentrated under reduced pressure. The residue was chromatographed on silica gel (10 mL column). Elution with 5% methanol in dichloromethane (100 mL) followed by 90:10:1 dichloromethane:methanol:ammonium hydroxide gave 0.028 g of α-(R)-(3-(S)-((4-(4-benzyl-5-methyl- 1H-pyrazol-3(2H)-on-2-yl)- piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid ESI-MS 571.4 (M+H); HPLC A: 2.61 min.

Workup

  1. concentrationthe mixture concentrated under reduced pressure
  2. customThe residue was chromatographed on silica gel (10 mL column)
  3. washElution with 5% methanol in dichloromethane (100 mL)

Sources & evidence

ORD record
ord-1d3dd34ae8964f6cbb8fa2a334464e32
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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