2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine → [(2S,3S,5R)-5-[2-amino-6-(azetidin-1-yl)purin-9-yl]-3-azido-tetrahydrofuran-2-yl]methanol

HRID 465724Notes

Reaction equation

HRID 465724 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4]([NH:21][CH2:22][CH:23]2[CH2:25]C2)[N:3]=1>C(OCC)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4]([N:21]2[CH2:22][CH2:23][CH2:25]2)[N:3]=1

Participants

3

Reactant 1

HCID 867461752-amino-9-(3-azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine

Product 1

HCID 476462[(2S,3S,5R)-5-[2-amino-6-(azetidin-1-yl)purin-9-yl]-3-azido-tetrahydrofuran-2-yl]methanolYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in a manner analogous to the preparation of 2-amino-9-(3-azido-2,3-dideoxy-β-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine (Example 15b). The reaction was worked up in an analogous manner except the combined ethyl acetate fractions were back washed with 150 mL of 1M potassium carbonate two times prior to chromatography. The product was isolated in 56% yield, 0.373 g, mp.=141°-143°C.

Workup

  1. washwere back washed with 150 mL of 1M potassium carbonate two times
  2. customThe product was isolated in 56% yield, 0.373 g, mp.=141°-143°C.

Sources & evidence

ORD record
ord-3873229ff0804545a778155c6d70ed81
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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