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

HRID 363410Notes

Reaction equation

HRID 363410 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 (D2O) 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-719420e417274afbacd787a7fea012bc
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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