HCID 86676481, compound → HCID 71246130, compound

HRID 1052324Notes

Reaction equation

HRID 1052324 reaction equation
[NH2:1][C@@H:2]([C:47](=[O:82])[NH:48][CH2:49][CH2:50][CH2:51][CH2:52][C@@H:53]([C:75]([O:77]C(C)(C)C)=[O:76])[NH:54][C:55](=[O:74])[NH:56][C@H:57]([C:67]([O:69]C(C)(C)C)=[O:68])[CH2:58][CH2:59][C:60]([O:62]C(C)(C)C)=[O:61])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:46])[CH2:9][N:10]1[CH2:21][CH2:20][N:19]([CH2:22][C:23](=[O:29])[O:24]C(C)(C)C)[CH2:18][CH2:17][N:16]([CH2:30][C:31](=[O:37])[O:32]C(C)(C)C)[CH2:15][CH2:14][N:13]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[CH2:12][CH2:11]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:1][C@H:2]([C:47](=[O:82])[NH:48][CH2:49][CH2:50][CH2:51][CH2:52][C@@H:53]([C:75]([OH:77])=[O:76])[NH:54][C:55](=[O:74])[NH:56][C@H:57]([C:67]([OH:69])=[O:68])[CH2:58][CH2:59][C:60]([OH:62])=[O:61])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:46])[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH2:38][C:39]([OH:41])=[O:40])[CH2:14][CH2:15][N:16]([CH2:30][C:31]([OH:37])=[O:32])[CH2:17][CH2:18][N:19]([CH2:22][C:23]([OH:29])=[O:24])[CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 86676481HCID 86676481, compound

Product 1

HCID 71246130HCID 71246130, compoundYield 5.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ((8R,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) in TFA (1.0 mL) and DCM (1.0 mL) was stirred at rt for overnight. The solvent was removed under a stream of nitrogen to give crude (8S,15S,19S)-8-amino-2,9,17-trioxo-1-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)-3,10,16,18-tetraazahenicosane-15,19,21-tricarboxylic acid (57.9 mg). A small amount (9 mg) crude product was purified by HPLC to give pure (8S,15S,19S)-8-amino-2,9,17-trioxo-1-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)-3,10,16,18-tetraazahenicosane-15,19,21-tricarboxylic acid (MIP-1457, (2.7 mg)) as a white solid. MS (ESI), 832.2 (M−H)−.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. customto give crude (8S,15S,19S)-8-amino-2,9,17-trioxo-1-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)-3,10,16,18-tetraazahenicosane-15,19,21-tricarboxylic acid (57.9 mg)
  3. customA small amount (9 mg) crude product was purified by HPLC

Sources & evidence

ORD record
ord-713978a62008477a8f43465c2e608e5a
Source dataset
uspto-grants-2016_07
Patent number
US09388144B2

Reaction notes

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