tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate → 3-((8-(3-(2-(tert-Butoxycarbonyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751052Notes

Reaction equation

HRID 1751052 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:51]=[CH:52][CH:53]=1)[CH2:14][N:15]1[C:19](=[O:20])[C:18]2([CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][N:29]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[C:30]3[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:22][CH2:21]2)[N:17]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:16]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:41]([O:40][C:38]([C:30]1[N:29]([CH2:28][CH2:27][CH2:26][N:23]2[CH2:22][CH2:21][C:18]3([N:17]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH2:16][N:15]([CH2:14][C:13]4[CH:12]=[C:11]([CH:53]=[CH:52][CH:51]=4)[C:9]([OH:10])=[O:8])[C:19]3=[O:20])[CH2:25][CH2:24]2)[C:37]2[C:32]([CH:31]=1)=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

4

Reactant 1

HCID 58046712tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate

Product 1

HCID 580466383-((8-(3-(2-(tert-Butoxycarbonyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 30.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate (0.27 g, 0.32 mmol) in MeOH (5 mL), was added 10%/wt palladium on carbon (0.080 g). The reaction mixture was hydrogenated at 50 psi for 48 hours. It was filtered over Celite, and isolated by preparatory thin layer chromatography in 10% methanol in dichloromethane to obtain the title compound (0.060 g, 30%); 1H NMR (DMSO-d6): δ 1.56 (s, 9H), 1.66 (d, 2H, J=14 Hz), 1.95 (t, 2H, J=6.4 Hz), 2.50-2.66 (m, 4H), 2.88 (bs, 4H), 4.59-4.64 (m, 6H), 6.78 (t, 1H, J=7.2 Hz), 6.88 (d, 2H, J=8.4 Hz), 7.10 (t, 1H, J=7.2 Hz), 7.19-7.31 (m, 3H), 7.48-7.54 (m, 2H), 7.67 (t, 2H, J=8.4 Hz), 7.87 (d, 2H, J=6.4 Hz), 8.13 (s, 1H), 12.75 (bs, 1H); MS for C37H42N4O5 m/z 623.16 (M+H)+.

Workup

  1. filtrationIt was filtered over Celite
  2. customisolated by preparatory thin layer chromatography in 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-cc3140ebf824418ab528fbd35acda1c8
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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