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Hydrochloric Acid → HCID 72793228, compound

HRID 1053481
Notes
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Reaction equation

HRID 1053481 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH2:54][C:55]([NH:57][CH2:58][C:59](O)=[O:60])=[O:56])[CH2:12][CH2:13][NH:14][C:15](=[O:53])[CH2:16][N:17]2[CH2:28][CH2:27][N:26]([CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25][CH2:24][N:23]([CH2:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:22][CH2:21][N:20]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:19][CH2:18]2)=[O:10])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.[C:73]1(=[O:82])[N:77]([CH2:78][CH2:79][NH2:80])[C:76](=[O:81])[CH:75]=[CH:74]1.Cl>CC#N>[O:82]=[C:73]1[CH:74]=[CH:75][C:76](=[O:81])[N:77]1[CH2:78][CH2:79][NH:80][C:59](=[O:60])[CH2:58][NH:57][C:55](=[O:56])[CH2:54][N:11]([C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH2:12][CH2:13][NH:14][C:15](=[O:53])[CH2:16][N:17]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:36])[CH2:25][CH2:24][N:23]([CH2:37][C:38]([O:39][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:44])[CH2:22][CH2:21][N:20]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2778791N-(2-Aminoethyl)maleimideHCID 72793227HCID 72793227, compound

Product 1

HCID 72793228HCID 72793228, compound

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a 50-mL round bottom flask loaded with 2-(2-(2-(4-hydroxyphenyl)-N-(2-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)ethyl)acetamido)acetamido)acetic acid 3 (0.113 g, 0.131 mmol) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.038 g, 0.198 mmol, 1.5 eq.) and 2-maleimidoethylamine.HCl (0.035 g, 0.198 mmol, 1.5 eq.). The mixture was dissolved in 10 mL of CH3CN and stirred for 12 hours at room temperature. After solvent removal in vacuo, purification was achieved by preparative reverse-phase HPLC (gradient from 100% 0.1% formic acid in water to 50% 0.1% formic acid in water/50% CH3CN) to give 4. 1H-NMR (300 MHz, CDCl3) δ 9.02 (m, 1H), 8.07 (m, 1H), 7.01 (m, 2H), 6.79 (m, 2H), 6.65 (s, 1H), 4.23-2.80 (m, 34H), 1.45 (s, 27H); 13C-NMR (75 MHz, CDCl3) δ 173.67, 173.43, 171.04, 170.33, 170.26, 170.08, 169.94, 169.86, 168.64, 156.55, 156.47, 134.16, 130.33, 130.06, 125.57, 125.09, 115.95, 115.84, 81.93, 81.87, 81.81, 81.70, 56.63, 56.08, 55.90, 53.12, 52.01, 50.95, 49.79, 49.41, 49.39, 47.22, 43.44, 43.07, 39.58, 39.15, 38.25, 38.10, 37.74, 37.34, 28.17.

Workup

  1. customAfter solvent removal
  2. customin vacuo, purification
  3. customto give 4

Sources & evidence

ORD record
ord-ffe60b67468d4a5397077f8bf6cf17d7
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09393327B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes