HCID 11749200, compound → HCID 454987, compound

HRID 2118088Notes

Reaction equation

HRID 2118088 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[CH2:15][O:14][C@@H:13]([CH2:16][O:17]C(=O)C3C=CC=CC=3)[O:12]2)=[C:4]([Cl:26])[N:3]=1.CO[Na].CO>CO>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4]([Cl:26])[N:3]=1

Participants

4

Reactant 2

HCID 11749200HCID 11749200, compoundHCID 178501943HCID 178501943, compound

Product 1

HCID 454987HCID 454987, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2 °C

Procedure

Benzoic acid 4(R)-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2(R)-ylmethyl ester (2.4 kg, 6.3 moles) and methanol (6.24 L) were combined under inert atmosphere. 25% MeONa/MeOH (33.6 g) was added at room temperature and the reaction mixture was stirred for 16-24 hours. The reaction was monitored by HPLC for complete deprotection of the benzoate ester. The reaction mixture was cooled to 2° C. for 2 hours. The solids were collected by filtration and dried in vacuo to give the desired compound (1.2 kg, 71% yield).

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-8569b1a5238940e392b0e198224bb8d4
Source dataset
uspto-grants-2008_10
Patent number
US07442813B2

Reaction notes

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