Ethanol → HCID 72793227, compound

HRID 1053480Notes

Reaction equation

HRID 1053480 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH2:54][C:55](=[O:63])[NH:56][CH2:57][C:58](=[O:62])[O:59]CC)[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:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24][N:23]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[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.O[Li].O.CCO>O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:11]([CH2:54][C:55]([NH:56][CH2:57][C:58]([OH:62])=[O:59])=[O:63])[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:31])[O:32][C:33]([CH3:35])([CH3:36])[CH3:34])[CH2:25][CH2:24][N:23]([CH2:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])[CH2:22][CH2:21][N:20]([CH2:45][C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[CH2:19][CH2:18]2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 72793158Tri-tert-butyl 2,2',2''-(10-(6-(2-(4-hydroxyphenyl)acetyl)-2,8,11-trioxo-12-oxa-3,6,9-triazatetradecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate

Product 1

HCID 72793227HCID 72793227, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50-mL round bottom flask loaded with tri-tert-butyl 2,2′,2″-(10-(6-(2-(4-hydroxyphenyl)acetyl)-2,8,11-trioxo-12-oxa-3,6,9-triazatetradecyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 2 (0.260 g, 0.291 mmol) was added LiOH.H2O (0.018 g, 0.437 mmol, 1.5 eq.), 6 mL of EtOH, and 2 mL of H2O. The reaction was stirred at room temperature for 12 hours. 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 3. 65.5% 1H-NMR (300 MHz, CDCl3) δ 8.66 (m, 1H), 8.07 (m, 1H), 7.02 (m, 2H), 6.29 (m, 2H), 6.34 (br s, 1H), 4.20-2.80 (m, 34H), 1.44 (s, 27H); 13C-NMR (75 MHz, CDCl3) δ 174.51, 174.14, 173.70, 173.45, 172.43, 169.80, 167.18, 156.59, 156.45, 130.43, 130.02, 125.93, 116.08, 115.89, 81.89, 81.85, 81.75, 56.42, 55.62, 52.76, 52.32, 51.61, 50.52, 49.67, 49.31, 49.25, 49.12, 47.69, 47.52, 43.54, 43.21, 40.37, 39.38, 38.07, 28.14.

Workup

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

Sources & evidence

ORD record
ord-83bac9cddc68420db70686c355374606
Source dataset
uspto-grants-2016_07
Patent number
US09393327B2

Reaction notes

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