Hydrochloric Acid → HCID 70174892, compound

HRID 2185478Notes

Reaction equation

HRID 2185478 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][C:11]([NH:13][C@H:14]1[CH2:18][N:17](C(OC(C)(C)C)=O)[C@H:16]([C:26]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:37][CH:36]=3)[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12])=O)(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[NH2:9][CH2:10][C:11]([NH:13][C@H:14]1[CH2:18][NH:17][C@H:16]([C:26]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:39][CH:40]=3)[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70176913HCID 70176913, compound

Product 1

HCID 70174892HCID 70174892, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (9 mL) was added to a solution of 1-[trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-Prolyl]-4-(4-benzyloxyphenoxy)piperidine (D, 330 mg) in 1,4-dioxane (9 mL) at room temperature. After stirring at room temperature for 30 min, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the titled compound (186 mg) as a white powder: 1H NMR (400 MHz, D2O) δ 1.58 (br s, 2H), 1.83 (br s, 2H), 2.25 (m, 1H), 2.43 (m, 1H), 3.20-3.40 (m, 3H), 3.50-3.70 (m, 3H), 3.70 (s, 2H), 4.41 (m, 1H), 4.85 (t, J=8.30 Hz, 1H), 4.93 (s, 2H), 6.85 (s, 4H), and 7.24-7.31 (m, 5H); mass spectrum (E+) m/e 452; IR (KBr) 3438, 3059, 1689, 1651, 1549, 1508, 1228, 1024, 825, 741, and 698 cm−1; Anal. Calcd for C25H32N4O4.2HCl.0.5H2O: C, 56.18; H, 6.60; N, 10.48; Cl, 13.27. Found: C, 56.56; H, 6.61; N, 10.05; Cl, 12.72.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-b1c247e674c04f1b8d824d407a88a54b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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