Acetic acid--N-[(1-{N-[14-amino-1,4,7,10,13-pentahydroxy-5-(2-methylpropyl)-2,8-di(propan-2-yl)-3,6,9,12-tetraazatetradeca-3,6,9,12-tetraen-1-ylidene]-5-hydroxy-5-iminonorvalyl}pyrrolidin-2-yl)(hydroxy)methylidene]glycine (1/1) → Larazotide

HRID 2172176Notes

Reaction equation

HRID 2172176 reaction equation
[CH3:1][CH:2]([CH2:4][C@H:5]([NH:36][C:37]([C@@H:39]([NH:43][C:44]([CH2:46][NH:47][C:48]([CH2:50][NH2:51])=[O:49])=[O:45])[CH:40]([CH3:42])[CH3:41])=[O:38])[C:6]([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:22]([N:24]1[C@H:28]([C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:17][CH2:18][C:19]([NH2:21])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])[CH3:3].CC(O)=O>O>[CH3:3][CH:2]([CH2:4][C@H:5]([NH:36][C:37]([C@@H:39]([NH:43][C:44]([CH2:46][NH:47][C:48]([CH2:50][NH2:51])=[O:49])=[O:45])[CH:40]([CH3:41])[CH3:42])=[O:38])[C:6]([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:22]([N:24]1[C@H:28]([C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])[CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:17][CH2:18][C:19]([NH2:21])=[O:20])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:7])[CH3:1]

Participants

3

Reactant 1

HCID 44146842Acetic acid--N-[(1-{N-[14-amino-1,4,7,10,13-pentahydroxy-5-(2-methylpropyl)-2,8-di(propan-2-yl)-3,6,9,12-tetraazatetradeca-3,6,9,12-tetraen-1-ylidene]-5-hydroxy-5-iminonorvalyl}pyrrolidin-2-yl)(hydroxy)methylidene]glycine (1/1)

Product 1

HCID 9810532Larazotide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solubilities of Larazotide acetate and the corresponding chloride salt in water were tested at 20° C. after 14 hours of vigorous stirring in the presence of residual solid. Concentrations of peptide are measured by standardized HPLC. The chloride salt is more soluble than the acetate salt.

Sources & evidence

ORD record
ord-1796805bfe664afeab2f1b5ea3d417a8
Source dataset
uspto-grants-2015_06
Patent number
US09051349B2

Reaction notes

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