4-[2-(N-Boc-N-methylamino)ethyl]benzoic acid → tert-Butyl (2-{4-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}ethyl)methylcarbamate

HRID 446544Notes

Reaction equation

HRID 446544 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:20])[CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]([F:75])([F:74])[C:23]1[CH:24]=[C:25]([CH:67]=[C:68]([C:70]([F:73])([F:72])[F:71])[CH:69]=1)[C:26]([N:28]1[CH2:32][C@@:31]([CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][C:45]3([C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[CH2:49][C@@H:48]3[O:56][CH2:57][C:58]([N:60]([CH3:66])[CH2:61][CH2:62][CH2:63][NH:64][CH3:65])=[O:59])[CH2:44][CH2:43]2)([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[O:30][CH2:29]1)=[O:27]>>[F:73][C:70]([F:71])([F:72])[C:68]1[CH:67]=[C:25]([CH:24]=[C:23]([C:22]([F:21])([F:75])[F:74])[CH:69]=1)[C:26]([N:28]1[CH2:32][C@@:31]([CH2:40][CH2:41][N:42]2[CH2:43][CH2:44][C:45]3([C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[CH2:49][C@@H:48]3[O:56][CH2:57][C:58]([N:60]([CH3:66])[CH2:61][CH2:62][CH2:63][N:64]([CH3:65])[C:15]([C:14]3[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][N:8]([CH3:20])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:19][CH:18]=3)=[O:17])=[O:59])[CH2:46][CH2:47]2)([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[O:30][CH2:29]1)=[O:27]

Participants

3

Reactant 2

HCID 666713624-[2-(N-Boc-N-methylamino)ethyl]benzoic acidHCID 866634192-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamide

Product 1

HCID 86663448tert-Butyl (2-{4-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}ethyl)methylcarbamateYield 92%

Procedure

The compound (140 mg, 0.501 mmol) obtained in Example 50a and the compound (260 mg, 334 mol) obtained in Example 1k were used to give the title compound (320 mg; yield, 92%) as a white solid according to the method described in Example 41a.

Sources & evidence

ORD record
ord-bbcea42410404bcd815290b0d54aadce
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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