HCID 131737100, compound → [(S)-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]-cyclopropyl-methyl]acetate

HRID 60709Notes

Reaction equation

HRID 60709 reaction equation
[C:1]([O:4][CH:5]([CH:26]1[CH2:28][CH2:27]1)[C@H:6]1[O:10][C@@H:9]([N:11]2[C:15]3[N:16]=[C:17]([NH2:20])[N:18]=[CH:19][C:14]=3[S:13][C:12]2=[O:21])[C@@H:8](CC([O-])=O)[CH2:7]1)(=[O:3])[CH3:2].C(OC([C@H]1O[C@@H](N2C3N=C(N)N=CC=3SC2=O)[C@@H](CC([O-])=O)C1)CC)(=[O:31])C>>[NH2:20][C:17]1[N:18]=[CH:19][C:14]2[S:13][C:12](=[O:21])[N:11]([C@@H:9]3[O:10][C@H:6]([C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH:26]4[CH2:27][CH2:28]4)[CH2:7][C@H:8]3[OH:31])[C:15]=2[N:16]=1

Participants

3

Reactant 2

HCID 131737100HCID 131737100, compound2×HCID 131737101HCID 131737101, compound

Product 1

HCID 121396321[(S)-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]-cyclopropyl-methyl]acetate

Procedure

The title compound was prepared in analogy to Example 4, by using [(2R,3R,5S)-5-[acetoxy(cyclopropyl)methyl]-2-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl] acetate (compound 16a) instead of [(2R,3R,5S)-5-(1-acetoxypropyl)-2-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-3-yl]acetate (compound 2a). Example 16 was purified and separated by preparative HPLC to afford Example 16-A and Example 16-B as white solid.

Workup

  1. customExample 16 was purified
  2. customseparated by preparative HPLC

Sources & evidence

ORD record
ord-169d8bebb0f44335a3a30c370b965408
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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