Diethyl Ether → HCID 178501476, compound

HRID 2121161Notes

Reaction equation

HRID 2121161 reaction equation
[CH3:1][O:2][C:3](=[O:48])[C@H:4]([CH2:44][CH2:45][S:46][CH3:47])[NH:5][C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:36])[C@H:14]([CH2:30][C:31]2[N:35]=[CH:34][NH:33][CH:32]=2)[N:15](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:9][C:8]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(OCC)C>Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:48])[C@H:4]([CH2:44][CH2:45][S:46][CH3:47])[NH:5][C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:36])[C@H:14]([CH2:30][C:31]2[N:35]=[CH:34][NH:33][CH:32]=2)[NH2:15])=[CH:9][C:8]=1[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 178501475HCID 178501475, compound

Product 1

HCID 178501476HCID 178501476, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

[4-(bis-tert-butoxycarbonyl-L-histidyl)-2-phenylbenzoyl methionine methyl ester (0.992 g, 1.42 mmol), prepared as in Example 184A, was dissolved in 4 M HCl/dioxane (15 mL), upon which gas evolution was observed. The clear amber solution was stirred for 6 hours, during which time a white precipitate formed. The mixture was treated with ethyl ether and the precipitate was isolated by filtration to provide 0.779 g (100%) of [4-(L-histidyl)-2-phenylbenzoyl methionine methyl ester (believed to be the mono-hydrochloride salt); 1H NMR (CD3OD) δ 1.72-1.87 (m, 1H), 1.95-2.03 (comp, 4H), 2.08-2.28 (comp, 2H), 3.38-3.60 (comp, 2H), 3.67 (s, 3H), 4.45-4.57 (comp, 2H), 7.30-7.46 (comp, 6H), 7.53 (d, 1H), 7.69 (d, 1H), 7.77 (app s, 1H), 8.90 (s, 1H). LRMS (CI): 496 (M+1)+.

Workup

  1. customformed
  2. customthe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-bfeb667819194c92947fd0c7df933e1c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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