N-(tert-Butoxycarbonyl)-1,5-diaminopentane → HCID 86674620, compound

HRID 1624854Notes

Reaction equation

HRID 1624854 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[O:7])(C)(C)C.[C:15]([C@@H:18]([NH:51][C:52]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][C:70]([OH:72])=[O:71])=[O:53])[CH2:19][CH2:20][C:21](=[O:50])[NH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][C:30](=[O:49])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38]C(ON1C(=O)CCC1=O)=O)([OH:17])=[O:16].CCN(C(C)C)C(C)C>C1COCC1>[NH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][NH:31][C:30]([CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][NH:22][C:21]([CH2:20][CH2:19][C@H:18]([NH:51][C:52]([CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][C:70]([OH:72])=[O:71])=[O:53])[C:15]([OH:17])=[O:16])=[O:50])=[O:49])=[O:7]

Participants

5

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 81531DiisopropylethylamineHCID 86644536Ste-Glu-AEEA-AEEA-OSU

Product 1

HCID 86674620HCID 86674620, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-tert-butoxycarbonyl cadaverine (24.3 mg; 0.12 mmol) was added to a solution of 17-((S)-1-Carboxy-3-{2-[2-({2-[2-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl methoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)-heptadecanoic acid (100 mg; 0.12 mmol) and DIPEA (46.68 mg; 0.36 mmol) in THF (2.0 ml). Reaction mixture was stirred over night at room temperature, and then concentrated in vacuo. The residue was dissolved in a mixture of water (5 ml) and THF (2 ml), and purified by preparative HPLC (RP18 column). Fractions containing the Boc-protected coupling product was pooled and taken to dryness. The residual was dissolved in 50% TFA-DCM (4 ml) and stirred for 1 h at room temperature, then concentrated in vacuo to provide 54 mg (55%) of the title material as its trifluoroacetic acid salt.

Workup

  1. customReaction mixture
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in a mixture of water (5 ml) and THF (2 ml)
  4. custompurified by preparative HPLC (RP18 column)
  5. additionFractions containing the Boc-protected coupling product
  6. dissolutionThe residual was dissolved in 50% TFA-DCM (4 ml)
  7. stirringstirred for 1 h at room temperature
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e72c6f7b26fb4f4a801654788dce550e
Source dataset
uspto-grants-2014_07
Patent number
US08779109B2

Reaction notes

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