Hydrogen Bromide → (2R)-2-amino-6-[4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-5-hydroxypyridin-1-ium-1-yl]hexanoate

HRID 1177

Reaction equation

[OH:1][C:2]1[CH:3]=[N+:4]([CH2:49][CH2:50][CH2:51][CH2:52][CH:53]([NH:61]C(OCC2C=CC=CC=2)=O)[C:54]([O:56]C(C)(C)C)=[O:55])[CH:5]=[C:6]([CH2:28][CH2:29][CH:30]([NH:38]C(OCC2C=CC=CC=2)=O)[C:31]([O:33]CCCC)=[O:32])[C:7]=1[CH2:8][CH:9]([NH:17]C(OCC1C=CC=CC=1)=O)[C:10]([O:12]C(C)(C)C)=[O:11].Br>>[CH:5]1[N+:4]([CH2:49][CH2:50][CH2:51][CH2:52][C@@H:53]([NH2:61])[C:54]([O-:56])=[O:55])=[CH:3][C:2]([OH:1])=[C:7]([CH2:8][C@H:9]([NH2:17])[C:10]([OH:12])=[O:11])[C:6]=1[CH2:28][CH2:29][C@H:30]([NH2:38])[C:31]([OH:33])=[O:32]

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 880120833-Hydroxy-1-(5-benzoxycarbonylamino-5-t-butoxycarbonyl-pentyl)-4-(2-benzyloxycarbonylamino-2-t-butoxycarbonyl-ethyl)-5-(3-benzyloxycarbonylamino-3-butoxycarbonylpropyl) pyridinium

Product 1

HCID 105071(2R)-2-amino-6-[4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-5-hydroxypyridin-1-ium-1-yl]hexanoate

Procedure

reacting the pyridinium salt prepared in step (c) with HBr in an appropriate solvent to provide deoxypyridinoline.

Sources & evidence

ORD record: ord-1c6890bb15744174b710f1c89858ac54
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723619

Linked notes

Loading…