Triethylamine → HCID 44299404, compound

HRID 1678037Notes

Reaction equation

HRID 1678037 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][C@@H:37]([C:42]([OH:44])=[O:43])[C:38]([SH:41])([CH3:40])[CH3:39])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])[C:15]([SH:18])([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(N(CC)CC)C>C(#N)C.O>[CH3:16][C:15]1([CH3:17])[S:18][S:41][C:38]([CH3:39])([CH3:40])[C@H:37]([C:42]([OH:44])=[O:43])[NH:36][C:34](=[O:35])[C@@H:26]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:25][C:23](=[O:24])[CH2:22][NH:21][C:19](=[O:20])[C@@H:14]1[NH:13][C:11]([C@@H:2]([NH2:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)=[O:12]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 9897563HCID 9897563, compound3×

Product 1

HCID 44299404HCID 44299404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

3.0 mg of DPDPE (Tyr-D-Pen-Gly-Phe-D-Pen) was dissolved in 5 ml of anhydrous acetonitrile. A 20% molar excess of PEG reagent (either mPEG-SPA 5K [27.9 mg] or mPEG-SPA 2K [11.1 mg]) and triethylamine (0.8μl) was added to the DPDPE. The reaction was allowed to proceed at room temperature under an argon atmosphere for 2 days. The sample was diluted to 15 ml with deionized water and lyophilized. The PEG-DPDPE powder was reconstituted in 5 ml of deionized water and purified on a Superdex 30 size exclusion column. The pertinent fractions were pooled together, dialyzed against water and frozen until in situ perfusion experiments.

Workup

  1. custompurified on a Superdex 30 size exclusion column
  2. customdialyzed against water
  3. temperaturefrozen until in situ perfusion experiments

Sources & evidence

ORD record
ord-05da944f8bae4af5b3d919496b42c79e
Source dataset
uspto-grants-2011_08
Patent number
US08008435B2

Reaction notes

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