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

HRID 2287819Notes

Reaction equation

HRID 2287819 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 6 N 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-bfe74405877645f19cf5d204c70abb84
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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