Hydrochloric Acid → Gly-Ala-DAla-Gly-Gly.HCl

HRID 976205Notes

Reaction equation

HRID 976205 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][C@@H:11]([C:13]([NH:15][CH2:16][C:17]([NH:19][CH2:20][C:21]([O:23]CC1C=CC=CC=1)=[O:22])=[O:18])=[O:14])[CH3:12])=[O:9])[CH3:7])=[O:4].[ClH:38]>C(O)(=O)C>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][C@@H:11]([C:13]([NH:15][CH2:16][C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])=[O:14])[CH3:12])=[O:9])[CH3:7])=[O:4].[ClH:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131719920Boc-Gly-Ala-DAla-Gly-Gly-OBzl

Product 1

HCID 131719918Gly-Ala-DAla-Gly-Gly.HClYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To Boc-Gly-Ala-DAla-Gly-Gly-OBzl prepared as in Example 33C (17.2 g, 33.0 mmol) in glacial acetic acid (480 ml) was added 6N HCl (120 ml) and the reaction mixture was stirred at room temperature for 24 h. Concentration in vacuo followed by coevaporation with water (2×250 ml) and toluene (2×250 ml) afforded 12.9 g (100% yield) of the product as a white powder: 1H NMR (D20) δ 1.36 (d, J=6.9 Hz, 3 H), 1.38 (d, J=7.2 Hz, 3 H), 3.84 (s, 2 H), 3.96 (s, 2 H), 3.99 (s, 2 H), 4.30-4.36 (m, 2 H).

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-34910a80ab2c448aa29a9d8ccac990c6
Source dataset
uspto-grants-1997_03
Patent number
US05610293

Reaction notes

Loading…