Hydrochloric Acid → HCID 131719923, compound

HRID 2287822Notes

Reaction equation

HRID 2287822 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@@H:15]([C:17]([NH:19][CH2:20][C:21]([O:23]CC1C=CC=CC=1)=[O:22])=[O:18])[CH3:16])=[O:13])=[O:9])[CH3:7])=[O:4].[ClH:31]>C(O)(=O)C>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([NH:14][C@@H:15]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH3:16])=[O:13])=[O:9])[CH3:7])=[O:4].[ClH:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131719925HCID 131719925, compound

Product 1

HCID 131719923HCID 131719923, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To Gly-Ala-Gly-DAla-Gly-OBzl prepared as in Example 34C (13.4 g, 25.7 mol) in glacial acetic acid (400 ml) was added concentrated HCl (100 ml) and the reaction mixture was stirred at room temperature for 24 h. The solution was concentrated in vacuo, dissolved in water (100 ml) and the resulting aqueous solution was washed with ether (2×50 ml) and concentrated again in vacuo. Drying at high vacuum afforded 9.70 g (100% yield) of the product as a white powder: 1H NMR (D2O) δ 1.38 (d, J=7.2 Hz, 3 H), 1.39 (d, J=7.2 Hz, 3 H), 3.84 (s, 2 H), 3.92 (s, 2 H), 3.96 (s, 2 H), 4.34 (m, 2 H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutiondissolved in water (100 ml)
  3. washthe resulting aqueous solution was washed with ether (2×50 ml)
  4. concentrationconcentrated again in vacuo
  5. customDrying at high vacuum

Sources & evidence

ORD record
ord-288f5412505e4b768dcad905089c3d55
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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