1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86676479, compound

HRID 1052322Notes

Reaction equation

HRID 1052322 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:14][C:15](=[O:34])[NH:16][C@@H:17]([CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH:35]1[C:47]2[CH:46]([CH2:48][O:49][C:50]([NH:52][C@@H:53]([CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62](=[O:100])[CH2:63][N:64]3[CH2:75][CH2:74][N:73]([CH2:76][C:77](=[O:83])[O:78][C:79]([CH3:82])([CH3:81])[CH3:80])[CH2:72][CH2:71][N:70]([CH2:84][C:85](=[O:91])[O:86][C:87]([CH3:90])([CH3:89])[CH3:88])[CH2:69][CH2:68][N:67]([CH2:92][C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[CH2:66][CH2:65]3)[C:54](O)=[O:55])=[O:51])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]=2[CH:38]=[CH:37][CH:36]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:35]1[C:47]2[CH:46]([CH2:48][O:49][C:50](=[O:51])[NH:52][C@@H:53]([CH2:57][CH2:58][CH2:59][CH2:60][NH:61][C:62](=[O:100])[CH2:63][N:64]3[CH2:65][CH2:66][N:67]([CH2:92][C:93](=[O:94])[O:95][C:96]([CH3:97])([CH3:98])[CH3:99])[CH2:68][CH2:69][N:70]([CH2:84][C:85](=[O:91])[O:86][C:87]([CH3:88])([CH3:89])[CH3:90])[CH2:71][CH2:72][N:73]([CH2:76][C:77]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:83])[CH2:74][CH2:75]3)[C:54](=[O:55])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[NH:14][C:15](=[O:34])[NH:16][C@H:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]=2[CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12086117HCID 12086117, compoundHCID 251942251,5-Bis(1,1-dimethylethyl) N-((((1S)-5-amino-1-((1,1-dimethylethoxy)carbonyl)pentyl)amino)carbonyl)-L-glutamate

Product 1

HCID 86676479HCID 86676479, compoundYield 136%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-di-tert-butyl 2-(3-((S)-6-amino-1-(tert-butoxy)-1-oxohexan-2-yl)ureido)pentanedioate (0.048 g, 0.10 mmol), (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)hexanoic acid (56 mg, 0.0607 mmol), EDCI (19 mg, 0.10 mmol), HOBt (13.5 mg, 0.10 mmol) and DIPEA (0.10 mL) in DCM (5.0 mL) was stirred at room temperature for 2 hrs. The solvent was evaporated to give a residue, which was purified by Biotage eluting with DCM to 10% MeOH in DCM to give (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-oxo ethyl)-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. MS (ESI), 697.0 (M+H)+.

Workup

  1. customThe solvent was evaporated
  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-d8907e4a7e134fc4a77e0710468bf5d2
Source dataset
uspto-grants-2016_07
Patent number
US09388144B2

Reaction notes

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