Triethylamine → 1-(2-{[6-({6-[{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]-1,3-benzothiazol-2-yl}amino)hexanoyl](methyl)amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446602Notes

Reaction equation

[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38]([OH:40])=O)[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[C:64]1([C:110]2[CH:115]=[CH:114][CH:113]=[CH:112][CH:111]=2)[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=1[NH:70][C:71](=[O:109])[O:72][CH:73]1[CH2:78][CH2:77][N:76]([CH2:79][CH2:80][N:81]([CH3:108])[C:82](=[O:107])[CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][NH:88][C:89]2[S:90][C:91]3[CH:97]=[C:96]([C:98](=[O:106])[N:99]([CH3:105])[CH2:100][CH2:101][CH2:102][NH:103][CH3:104])[CH:95]=[CH:94][C:92]=3[N:93]=2)[CH2:75][CH2:74]1>>[C:64]1([C:110]2[CH:115]=[CH:114][CH:113]=[CH:112][CH:111]=2)[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=1[NH:70][C:71](=[O:109])[O:72][CH:73]1[CH2:74][CH2:75][N:76]([CH2:79][CH2:80][N:81]([C:82](=[O:107])[CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][NH:88][C:89]2[S:90][C:91]3[CH:97]=[C:96]([C:98](=[O:106])[N:99]([CH2:100][CH2:101][CH2:102][N:103]([C:38](=[O:40])[CH2:37][O:36][C@@H:28]4[C:25]5([CH2:24][CH2:23][N:22]([CH2:21][CH2:20][C@:11]6([C:13]7[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=7)[O:10][CH2:9][N:8]([C:6](=[O:7])[C:5]7[CH:41]=[C:42]([C:44]([F:46])([F:47])[F:45])[CH:43]=[C:3]([C:2]([F:1])([F:49])[F:48])[CH:4]=7)[CH2:12]6)[CH2:27][CH2:26]5)[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH2:29]4)[CH3:104])[CH3:105])[CH:95]=[CH:94][C:92]=3[N:93]=2)[CH3:108])[CH2:77][CH2:78]1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 62493Pivaloyl chloride

HCID 86663420{[(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}acetic acid

HCID 867619191-[2-(Methyl{6-[(6-{methyl[3-(methylamino)propyl]carbamoyl}-1,3-benzothiazol-2-yl)amino]hexanoyl}amino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate

Product 1

HCID 867619201-(2-{[6-({6-[{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]-1,3-benzothiazol-2-yl}amino)hexanoyl](methyl)amino}ethyl)piperidin-4-yl biphenyl-2-ylcarbamateYield 24.1%

Procedure

The compound (101 mg, 0.146 mmol) obtained in Example 1j, triethylamine (23 μL, 0.167 mmol), pivaloyl chloride (18 μL, 0.144 mmol) and the compound (101 mg, 0.139 mmol) obtained in Example 93d were used to give the title compound (47 mg; yield, 24%) as a white solid according to the method described in Example 92c.

Sources & evidence

ORD record: ord-456b238974a644c7b68fd955f48412b9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476253B2

Reaction notes

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