Ammonia → HCID 86607313, compound

HRID 552710Notes

Reaction equation

HRID 552710 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][CH2:22][S:23](Cl)(=[O:25])=[O:24])[O:12]1.[NH3:27]>CN(C)C=O.CO>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([CH2:21][CH2:22][S:23]([NH2:27])(=[O:25])=[O:24])[O:12]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86607310HCID 86607310, compound

Product 1

HCID 86607313HCID 86607313, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2-[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethanesulfonyl chloride (100.0 mg, 0.0002362 mol) was dissolved in N,N-Dimethylformamide (2.0 mL). 7.00 M of Ammonia in Methanol (0.500 mL) was added at 0° C. and the mixture was stirred for 30 minutes, allowing to warm to room temperature. The reaction was concentrated in vacuo and the residue was diluted with brine and extracted with EtOAc. The organic phase was brine washed, water washed and evaporated. The residue was purified by flash chromatography (0 to 100% EtOAc/Hexanes) to yield the product (40 mg, 42%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe residue was diluted with brine
  3. extractionextracted with EtOAc
  4. washwashed
  5. washwater washed
  6. customevaporated
  7. customThe residue was purified by flash chromatography (0 to 100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e78391b8371449e993f9e449385ec03e
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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