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

HRID 54127Notes

Reaction equation

HRID 54127 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:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:10]=[C:11]2[CH2:20][NH:21][C:22](=[O:38])[C@H:23]([CH3:37])[NH:24][C:25](=[O:36])[C@H:26]([CH3:35])[NH:27]C(OC(C)(C)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:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH:10]=[C:11]2[CH2:20][NH:21][C:22](=[O:38])[C@H:23]([CH3:37])[NH:24][C:25](=[O:36])[C@H:26]([CH3:35])[NH2:27])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 700929565,6-Bis(acetoxy)-1-(N-t-butoxycarbonyl-alanyl-alanyl)aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride

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-dihydronaphthalene 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), 7.07 (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-02510925554548978913a0a659317079
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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