Triethylamine → HCID 86751111, compound

HRID 266021Notes

Reaction equation

HRID 266021 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:46]([OH:48])=[O:47])[NH:17][C:18](=[O:45])[CH2:19][CH2:20][C@H:21]([C@@H:23]2[C@:40]3([CH3:41])[C@H:26]([C@H:27]4[C@H:37]([CH2:38][C@@H:39]3[OH:42])[C@:35]3([CH3:36])[C@@H:30]([CH2:31][C@H:32]([OH:43])[CH2:33][CH2:34]3)[CH2:29][C@H:28]4[OH:44])[CH2:25][CH2:24]2)[CH3:22])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:50]1(C)C=CC(S(O)(=O)=O)=CC=1.CCN(CC)CC>CO>[CH3:50][O:47][C:46](=[O:48])[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10])[NH:17][C:18](=[O:45])[CH2:19][CH2:20][C@H:21]([C@@H:23]1[C@:40]2([CH3:41])[C@H:26]([C@H:27]3[C@H:37]([CH2:38][C@@H:39]2[OH:42])[C@:35]2([CH3:36])[C@@H:30]([CH2:31][C@H:32]([OH:43])[CH2:33][CH2:34]2)[CH2:29][C@H:28]3[OH:44])[CH2:25][CH2:24]1)[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 86751112HCID 86751112, compound

Product 1

HCID 86751111HCID 86751111, compoundYield 429.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N6 -(phenylmethoxy)carbonyl-N2 -[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine 27.5 g) in MeOH (600 ml), kept at room temperature and under nitrogen atmosphere, was added to p-toluenesulfonic acid monohydrate (1.56 g; 8.2 mmol). After 20 h the reaction mixture was added to Et3N (0.832 g; 8.2 mmol). The mixture was evaporated under reduced pressure and the resulting crude was purified by flash chromatography to obtain the desired product (24.1 g; 35.2 mmol).

Workup

  1. customkept at room temperature and under nitrogen atmosphere
  2. customThe mixture was evaporated under reduced pressure
  3. customthe resulting crude was purified by flash chromatography

Sources & evidence

ORD record
ord-38af80897c4842f68042756d258961ee
Source dataset
uspto-grants-1997_07
Patent number
US05649537

Reaction notes

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