Hydrochloric Acid → 5,6-Bis(acetoxy)-1-(alanyl-alanyl)aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride

HRID 233390Notes

Reaction equation

HRID 233390 reaction equation
[ClH:1].[C:2]([O:5][C:6]1[C:15]([O:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH:9]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:10][C:11]2([CH2:22][NH:23][C:24](=[O:40])[C@H:25]([CH3:39])[NH:26][C:27](=[O:38])[C@H:28]([CH3:37])[NH:29]C(OC(C)(C)C)=O)C=O)(=[O:4])[CH3:3].Cl>C(OCC)C>[ClH:1].[C:2]([O:5][C:6]1[C:15]([O:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH:9]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:10]=[C:11]2[CH2:22][NH:23][C:24](=[O:40])[C@H:25]([CH3:39])[NH:26][C:27](=[O:38])[C@H:28]([CH3:37])[NH2:29])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86750151HCID 86750151, compound

Product 1

HCID 677047095,6-Bis(acetoxy)-1-(alanyl-alanyl)aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5,6-Bis(acetoxy)-1-(N-t-butoxycarbonyl-alanyl-alanyl)aminomethyl-3-phenyl-3,4-dihydronaphthal hydrochloride (2.00 g, 3.36 mmol) from Step 1 was dissolved in 25 mL of diethyl ether. The resultant solution was cooled and saturated with hydrogen chloride. The solution was stirred at ambient temperature for 3 h. The precipitate was filtered and washed thoroughly with dry diethyl ether. The solid was dried overnight at 60° C. in vacuo to give 1.69 g (95% yield) of the title compound as an off-white solid, m.p. 145°-161° C. (dec); 1H NMR (CDCl3) δ: 1.35 (dd, 3H), 1.41 (m, 3H), 2.23 (s, 3H), 2.26 (s, 3H), 2.70 (dt, 1H), 2.95 (dd, 1H), 3.69 (br s, 1H), 3.89 (dq, 1H), 4.17-4.45 (m, 3H), 6.11 (d, 1H), 7.0 (d, 1H), 7.25 (m, 6H), 8.27 (m, 1H). Analysis calculated for C27H33N3O6 +1.3HCl: C, 59.73; H, 6.37; N, 7.74. Found: C, 59.94; H, 6.08; N, 7.64.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed thoroughly with dry diethyl ether
  3. customThe solid was dried overnight at 60° C. in vacuo

Sources & evidence

ORD record
ord-be756992723d4c3dbf44f3d3326d5e5e
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Reaction notes

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