HCID 24176, compound → Paromomycin

HRID 1631424Notes

Reaction equation

HRID 1631424 reaction equation
[CH2:1]1[C@H:6]([NH2:7])[CH:5]([O:8][C@H:9]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][CH:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42].C(Cl)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>>[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@H:9]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[NH2:19])[C@H:4]([O:20][C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([O:28][C@H:29]3[O:34][C@@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]3[NH2:39])[C@H:22]2[OH:40])[C@@H:3]([OH:41])[C@@H:2]1[NH2:42]

Participants

3

Reactant 2

HCID 24176HCID 24176, compoundHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 165580Paromomycin

Procedure

Starting with paromomycin I, the procedure described in WO2007/064954 is followed to generate the aldehyde 212L. b) Reductive amination is performed using general procedure 15 to generate the amine 212M. c) Fmoc protection of the amine is performed in the standard manner with Fmoc-Cl to generate 212N. d) 212N is deprotected as described in WO2007/064954 to generate 212O. e) 212O is sulfated using general procedure 1 to yield 212P. f) The sulfated paramomycin 212P is deprotected and converted to the azide as described in example 19 to generate 212Q.

Sources & evidence

ORD record
ord-6510aa5e448a44918a605628e52f4603
Source dataset
uspto-grants-2014_07
Patent number
US08791245B2

Reaction notes

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