Hydrochloric Acid → HCID 86759487, compound

HRID 1883551Notes

Reaction equation

HRID 1883551 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[C@H:23]2[C@@H:27]3[O:28][C:29]([CH3:32])([CH3:31])[O:30][C@@H:26]3[C@@H:25]([C:33]([OH:35])=O)[O:24]2)=[C:16]([NH:36][CH2:37][CH:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:15]=1.[CH3:51][NH:52][O:53][CH3:54].Cl.[OH-].[Na+]>ClCCl>[CH3:54][O:53][N:52]([CH3:51])[C:33]([C@@H:25]1[C@@H:26]2[C@@H:27]([O:28][C:29]([CH3:31])([CH3:32])[O:30]2)[C@H:23]([N:20]2[CH:19]=[N:18][C:17]3[C:21]2=[N:22][C:14]([Cl:13])=[N:15][C:16]=3[NH:36][CH2:37][CH:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:24]1)=[O:35]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14232N,O-DimethylhydroxylamineHCID 14798Sodium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86759123HCID 86759123, compound

Product 1

HCID 86759487HCID 86759487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Carbonyl di-imidazole (2.37 g, 14.6 mmol) was added to a stirring solution of (3aS,4S,6R,6aR)-6-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (prepared by following the method of Preparation 4 in International Patent Application No. WO94/17090) (6.015 g, 11.23 mmol) in dry dichloromethane (30 ml) under nitrogen. Mixture was stirred for 1 h. A dichloromethane solution of N,O-dimethylhydroxylamine (25.8 mmol; generated by basification of a 10 ml aqueous solution of 2.57 g of the corresponding hydrochloride at 0° C. with aqueous sodium hydroxide, followed by extraction with 3×5 ml dichloromethane and dried over sodium sulphate) was added. Mixture was stirred at room temperature for 60 h, quenched with aqueous citric acid (10% w/v, 40 ml). Organic solution was separated, washed with aqueous sodium bicarbonate (8% w/v, 40 ml), dried (sodium sulphate) and filtered. Removal of solvent in vacuo gave the title compound as a creamy white foam (6.66 g). TLC (100% ethyl acetate, visualised under an UV lamp) rf=0.51.

Workup

  1. customprepared
  2. customthe method of Preparation 4 in International Patent Application No
  3. extractionfollowed by extraction with 3×5 ml dichloromethane
  4. dry with materialdried over sodium sulphate)
  5. additionwas added
  6. stirringMixture was stirred at room temperature for 60 h
  7. customquenched with aqueous citric acid (10% w/v, 40 ml)
  8. customOrganic solution was separated
  9. washwashed with aqueous sodium bicarbonate (8% w/v, 40 ml)
  10. dry with materialdried (sodium sulphate)
  11. filtrationfiltered
  12. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-e51aae21757749aca30269d6d54ecce2
Source dataset
uspto-grants-2004_07
Patent number
US06762170B1

Reaction notes

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