Piperidine → HCID 86676480, compound

HRID 1052323Notes

Reaction equation

HRID 1052323 reaction equation
C1C2C(COC(=O)[NH:17][C@@H:18]([CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:60](=[O:98])[CH2:61][N:62]3[CH2:73][CH2:72][N:71]([CH2:74][C:75](=[O:81])[O:76][C:77]([CH3:80])([CH3:79])[CH3:78])[CH2:70][CH2:69][N:68]([CH2:82][C:83](=[O:89])[O:84][C:85]([CH3:88])([CH3:87])[CH3:86])[CH2:67][CH2:66][N:65]([CH2:90][C:91]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])=[O:92])[CH2:64][CH2:63]3)[C:19](=[O:54])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[NH:26][C:27](=[O:46])[NH:28][C@H:29]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:17][C@H:18]([C:19](=[O:54])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@@H:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[NH:26][C:27](=[O:46])[NH:28][C@H:29]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:55][CH2:56][CH2:57][CH2:58][NH:59][C:60](=[O:98])[CH2:61][N:62]1[CH2:73][CH2:72][N:71]([CH2:74][C:75](=[O:81])[O:76][C:77]([CH3:80])([CH3:79])[CH3:78])[CH2:70][CH2:69][N:68]([CH2:82][C:83](=[O:89])[O:84][C:85]([CH3:88])([CH3:87])[CH3:86])[CH2:67][CH2:66][N:65]([CH2:90][C:91]([O:93][C:94]([CH3:95])([CH3:96])[CH3:97])=[O:92])[CH2:64][CH2:63]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86676479HCID 86676479, compound

Product 1

HCID 86676480HCID 86676480, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5S,12S,16S)-tri-tert-butyl 1-(9H-fluoren-9-yl)-3,6,14-trioxo-5-(4-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)butyl)-2-oxa-4,7,13,15-tetraazaoctadecane-12,16,18-tricarboxylate (115 mg) containing some impurity in DMF (0.30 mL) and piperidine (0.30 mL) was stirred at rt for 1 hr. Solvents were evaporated under reduced pressure to give a residue, which was purified by Biotage eluting with DCM to 10% MeOH in DCM to give (8S,15S,19S)-tri-tert-butyl 8-amino-2,9,17-trioxo-1-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)-3,10,16,18-tetraazahenicosane-15,19,21-tricarboxylate (64 mg, 90%) as a colorless oil. MS (ESI), 1171.6 (M+H)+.

Workup

  1. customSolvents were evaporated under reduced pressure
  2. customto give a residue, which
  3. customwas purified by Biotage
  4. washeluting with DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-71594bf1467e4a2fb7da00d3fcb646b2
Source dataset
uspto-grants-2016_07
Patent number
US09388144B2

Reaction notes

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