Dimethylformamide → HCID 69827476, compound

HRID 2297660Notes

Reaction equation

HRID 2297660 reaction equation
Cl[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]([C:21](O)=[O:22])[O:12]1.[OH:24][N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[N:26]1.Cl.C[N:36](C)CCCN=C=NCC.[C:46](CC(=NO)N)([CH3:49])([CH3:48])[CH3:47].C(=O)(O)[O-].[Na+].C[N:61]([CH3:64])C=O>>[C:46]([C:64]1[N:61]=[C:21]([C@@H:13]2[C@@H:14]3[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]3[C@H:11]([N:6]3[CH:5]=[N:4][C:3]4[C:7]3=[N:8][CH:9]=[N:10][C:2]=4[O:24][N:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[N:27]=[N:26]3)[O:12]2)[O:22][N:36]=1)([CH3:49])([CH3:48])[CH3:47]

Participants

7

Reactant 6

HCID 6228Dimethylformamide2×HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14374715HCID 14374715, compoundHCID 57242918HCID 57242918, compound

Product 1

HCID 69827476HCID 69827476, compound

Conditions

Temperature
20 °C

Procedure

To a solution of (3aS,4S,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (10 g) in dimethylformamide (200 ml) was added 1-hydroxybenzotriazole (3.96 g) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (5.62 g). t-Butylacetamidoxime (3.40 g) in dimethylformamide (30 ml) was added and the mixture was stirred at 20° C. for 24 h under nitrogen. The mixture was then heated at 70° C. for a further 36 h. The resulting mixture was then cooled to 20° C., basified with a saturated solution of sodium bicarbonate (200 ml) and extracted with ethyl acetate (2×15 ml). The organic layers were washed with brine (300 ml), dried (MgSO4), evaporated to dryness in vacuo and triturated with ether to give a yellow solid (11.08 g). Purification by chromatography on silica gel, eluting with ethyl acetate cyclohexane (3:7), afforded the title compound (4.75 g) as a white solid.

Workup

  1. temperatureThe mixture was then heated at 70° C. for a further 36 h
  2. temperatureThe resulting mixture was then cooled to 20° C.
  3. extractionextracted with ethyl acetate (2×15 ml)
  4. washThe organic layers were washed with brine (300 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness in vacuo
  7. customtriturated with ether

Sources & evidence

ORD record
ord-0cac939178a647a28da7aac1e0caa342
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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