(14S,18S)-tri-tert-butyl 1-(1-(2-(bis(2-(tert-butoxy)-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylate → (14S,18S)-1-(1-(2-(bis(carboxymethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylic acid

HRID 1422510Notes

Reaction equation

HRID 1422510 reaction equation
C([O:5][C:6](=[O:125])[CH2:7][N:8]([CH2:117][C:118](=[O:124])[O:119]C(C)(C)C)[C:9](=[O:116])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16][N:17]([CH2:59][C:60]1[CH:65]=[CH:64][C:63]([O:66][CH2:67][C:68]2[N:69]=[N:70][N:71]([CH2:73][CH2:74][CH2:75][NH:76][C:77](=[O:115])[CH2:78][N:79]3[CH2:90][CH2:89][N:88]([CH2:91][C:92](=[O:98])[O:93]C(C)(C)C)[CH2:87][CH2:86][N:85]([CH2:99][C:100](=[O:106])[O:101]C(C)(C)C)[CH2:84][CH2:83][N:82]([CH2:107][C:108]([O:110]C(C)(C)C)=[O:109])[CH2:81][CH2:80]3)[CH:72]=2)=[CH:62][CH:61]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:58])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@@H:29]([C:51]([O:53]C(C)(C)C)=[O:52])[NH:30][C:31](=[O:50])[NH:32][C@H:33]([C:43]([O:45]C(C)(C)C)=[O:44])[CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:118]([CH2:117][N:8]([CH2:7][C:6]([OH:125])=[O:5])[C:9](=[O:116])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16][N:17]([CH2:59][C:60]1[CH:61]=[CH:62][C:63]([O:66][CH2:67][C:68]2[N:69]=[N:70][N:71]([CH2:73][CH2:74][CH2:75][NH:76][C:77](=[O:115])[CH2:78][N:79]3[CH2:90][CH2:89][N:88]([CH2:91][C:92]([OH:98])=[O:93])[CH2:87][CH2:86][N:85]([CH2:99][C:100]([OH:106])=[O:101])[CH2:84][CH2:83][N:82]([CH2:107][C:108]([OH:110])=[O:109])[CH2:81][CH2:80]3)[CH:72]=2)=[CH:64][CH:65]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:58])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C@@H:29]([C:51]([OH:53])=[O:52])[NH:30][C:31](=[O:50])[NH:32][C@H:33]([C:43]([OH:45])=[O:44])[CH2:34][CH2:35][C:36]([OH:38])=[O:37])([OH:124])=[O:119]

Participants

4

Reactant 1

HCID 86676474(14S,18S)-tri-tert-butyl 1-(1-(2-(bis(2-(tert-butoxy)-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylate

Product 1

HCID 86676475(14S,18S)-1-(1-(2-(bis(carboxymethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ((14S,18S)-tri-tert-butyl 1-(1-(2-(bis(2-(tert-butoxy)-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylate (21 mg, 0.012 mmol) in TFA (2.0 mL) and DCM (2.0 mL) was stirred at rt overnight. The solvent was removed under a stream of nitrogen to give a crude ((14S,18S)-1-(1-(2-(bis(carboxymethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)-8,16-dioxo-2-(4-((1-(3-(2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)propyl)-1H-1,2,3-triazol-4-yl)methoxy)benzyl)-2,9,15,17-tetraazaicosane-14,18,20-tricarboxylic acid, (MIP-1459), which was dissolved in ammonium acetate (0.30 mL, 0.50 N) solution in water (0.50 mL) with InCl3 (10 mg). The reaction mixture was heated at

Workup

  1. customThe solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-fcbece97cf3f4686932bf8b2634b338f
Source dataset
uspto-grants-2015_01
Patent number
US08926944B2

Reaction notes

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