(4-Nitrophenyl)acetic acid → 2-{[(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-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamide

HRID 446548Notes

Reaction equation

HRID 446548 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:14][C:15]([F:68])([F:67])[C:16]1[CH:17]=[C:18]([CH:60]=[C:61]([C:63]([F:66])([F:65])[F:64])[CH:62]=1)[C:19]([N:21]1[CH2:25][C@@:24]([CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][C:38]3([C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42][C@@H:41]3[O:49][CH2:50][C:51]([N:53]([CH3:59])[CH2:54][CH2:55][CH2:56][NH:57][CH3:58])=[O:52])[CH2:37][CH2:36]2)([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[O:23][CH2:22]1)=[O:20]>>[F:66][C:63]([F:64])([F:65])[C:61]1[CH:60]=[C:18]([CH:17]=[C:16]([C:15]([F:14])([F:68])[F:67])[CH:62]=1)[C:19]([N:21]1[CH2:25][C@@:24]([CH2:33][CH2:34][N:35]2[CH2:36][CH2:37][C:38]3([C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42][C@@H:41]3[O:49][CH2:50][C:51]([N:53]([CH3:59])[CH2:54][CH2:55][CH2:56][N:57]([CH3:58])[C:11](=[O:13])[CH2:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)=[O:52])[CH2:39][CH2:40]2)([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[O:23][CH2:22]1)=[O:20]

Participants

3

Reactant 2

HCID 4661(4-Nitrophenyl)acetic 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 866634512-{[(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-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamideYield 94.2%

Procedure

(4-Nitrophenyl)acetic acid (52 mg, 0.287 mmol) and the compound (186 mg, 0.239 mmol) obtained in Example 1k were used to give the title compound (212 mg; yield, 94%) as a colorless oily substance according to the method described in Example 41a.

Sources & evidence

ORD record
ord-87834bdd39d147cab3b582a169233697
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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