HCID 137190217, compound → HCID 137108719, compound

HRID 60708Notes

Reaction equation

HRID 60708 reaction equation
C([O:4][CH:5]([CH:27]1[CH2:29][CH2:28]1)[C@H:6]1[O:10][C@@H:9]([N:11]2[C:15]3[N:16]=[C:17]([NH2:21])[NH:18][C:19](=[O:20])[C:14]=3[S:13][C:12]2=[O:22])[C@@H:8](CC([O-])=O)[CH2:7]1)(=O)C.C(OC([C@H]1O[C@@H](N2C3N=C(N)NC(=O)C=3SC2=O)[C@@H](CC([O-])=O)C1)CC)(=[O:32])C>>[NH2:21][C:17]1[NH:18][C:19](=[O:20])[C:14]2[S:13][C:12](=[O:22])[N:11]([C@H:9]3[C@H:8]([OH:32])[CH2:7][C@@H:6]([CH:5]([CH:27]4[CH2:29][CH2:28]4)[OH:4])[O:10]3)[C:15]=2[N:16]=1

Participants

3

Reactant 2

HCID 137190217HCID 137190217, compound2×HCID 137190218HCID 137190218, compound

Product 1

HCID 137108719HCID 137108719, compound

Procedure

The title compound was prepared in analogy to Example 1, by using [(2R,3R,5S)-5-[acetoxy(cyclopropyl)methyl]-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate (compound 14b) instead of [(2R,3R,5S)-5-(1-acetoxypropyl)-2-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate (compound 1g). Example 14 was purified and separated by preparative HPLC to afford Example 14-A and Example 14-B as white solid.

Workup

  1. customExample 14 was purified
  2. customseparated by preparative HPLC

Sources & evidence

ORD record
ord-01cddf9516bc4f0ba933478753d87419
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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