Methanol → HCID 131720834, compound

HRID 2394263Notes

Reaction equation

HRID 2394263 reaction equation
S(O)(O)(=O)=O.N[C:7](=N)NCCCCN.[OH-:15].C[N+](C)(C)C.[CH3:21][C@@H:22]([C@@H:29]1[C@@:33]2([CH3:51])[CH2:34][CH2:35][CH:36]3[C@@:41]4([CH3:50])[CH2:42][CH2:43][CH:44]([O:46][C:47](Cl)=[O:48])[CH2:45][C:40]4=[CH:39][CH2:38][CH:37]3[CH:32]2[CH2:31][CH2:30]1)[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27].[CH3:52][OH:53]>CN(C=O)C>[C:47]([OH:46])(=[O:48])[CH3:7].[C:52]([CH2:28][CH:26]([CH2:25][CH2:24][CH2:23][C@H:22]([C@@H:29]1[C@:33]2([CH3:51])[C@H:32]([C@H:37]3[C@H:36]([CH2:35][CH2:34]2)[C@:41]2([CH3:50])[C:40]([CH2:45][C@H:44]([CH2:43][CH2:42]2)[OH:46])=[CH:39][CH2:38]3)[CH2:31][CH2:30]1)[CH3:21])[CH3:27])([OH:53])=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 60966Tetramethylammonium hydroxideHCID 54236888C28H45ClO2HCID 178512970HCID 178512970, compound

Product 1

HCID 131720834HCID 131720834, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Agmatine sulfate (100 mg, 0.438 mmol) was treated by tetramethylamonium hydroxide (158 mg, 0.876 mmol) in methanol (15 ml) for 1 h. The solvent was removed under reduced pressure. A suspension solution of the residue and cholesteryl chloroformate (197 mg, 0.438 mmol) in DMF (15 ml) was stirred at room temperature for 3 days. Filtration of the reaction mixture gave the crude product as a light yellow solid, which was purified by a silica gel column using chloroform-methanol-acetic acid (10:2:1) as eluent to yield the agmatinyl carboxycholesterol acetic acid salt as a white solid. 1H NMR (300 MHz, CD3OD): δ5.27 (broad s, 1 H), 4.65 (broad m, 1 H), 3.06 (t, 2 H), 2.99 (t, 2 H), 2.21 (broad d, 2 H), 1.95-0.65 (m, 31 H), 1.80 (s, 4 H), 0.91 (s, 3 H), 0.82 (d, 3 H), 0.76 (s, 3 H), 0.74 (s, 3 H), 0.59 (s, 3 H). LSIMS (NBA): m/e 543.4 for M+(C33H59N4O2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationFiltration of the reaction mixture
  3. customgave the crude product as a light yellow solid, which
  4. customwas purified by a silica gel column

Sources & evidence

ORD record
ord-db35c334250440cf91b11934833e9af8
Source dataset
uspto-grants-1998_09
Patent number
US05811406

Reaction notes

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