Chlorotrimethylsilane → HCID 135533268, compound

HRID 1720543Notes

Reaction equation

HRID 1720543 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[C:23]2[N:22]=[C:20]([NH2:21])[NH:19][C:17](=[O:18])[C:16]=2[N:15]=[CH:14]1)[CH2:2][CH3:3].C[Si](Cl)(C)C.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31].[NH4+].[OH-]>N1C=CC=CC=1.O>[C:29]([NH:21][C:20]1[NH:19][C:17](=[O:18])[C:16]2[N:15]=[CH:14][N:13]([C:23]=2[N:22]=1)[C@@H:6]1[O:7][C@H:8]([CH2:11][OH:12])[C@@H:9]([OH:10])[C@H:5]1[O:4][CH2:1][CH2:2][CH3:3])(=[O:33])[CH:30]([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 14923Ammonium HydroxideHCID 62325Isobutyryl chlorideHCID 135494296HCID 135494296, compound

Product 1

HCID 135533268HCID 135533268, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2'-O-Propylguanosine (3.6 gm) in pyridine (50 ml) was cooled in an ice bath and trimethylsilyl chloride (8.4 ml, 6 eq.) was added. The reaction mixture was stirred for 30 min and isobutyryl chloride (5.8 ml, 5 eq.) was added. The solution was stirred for 4 hours during which it was allowed to warm to room temperature. The solution was cooled, H2O added (10 ml) and the solution was stirred for an additional 30 mins. Concentrated NH4OH (10 ml) was added and the solution evaporated in vacuo. The residue was purified by silica gel chromatography using 10% MeOH/CH2CL2 to elute the product. Product-containing fractions were evaporated to yield 2.5 g of product as a foam. An analytical sample was re-chromatographed on silica and eluted with CH2Cl2 →6% MeOH/CH2Cl2. 1H NMR (DMSO-d6) δ 0.75 (t 3, CH3) 1.13 [d, 6, CH(CH3)2 ], 1.4 (m, 2, CH2), 2.75 [m, 1, CH(CH3)2 ], 3.52 (m, 6, OCH2), 3.36 and 3.6 (ABX, 2, H-5'), 3.95 (m, 1), 4.26 (m, 1), 4.33 (m, 1), 5.07 (t, 1, 5'-OH), 5.18 (d, 1, 3'-OH), 5.9 (d, 1, H-1'), 8.25 (s, 1, H-8), 11.65 (br s, 1, NH) and 12.1 (br s, 1, NH). Anal. Calcd. for C17H25N5O6.1/2H2O: C, 50.49; H, 6.48; N, 17.32. Found: C, 50.81; H, 6.62; N, 17.04.

Workup

  1. stirringThe solution was stirred for 4 hours during which it
  2. temperatureThe solution was cooled
  3. stirringthe solution was stirred for an additional 30 mins
  4. customthe solution evaporated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washto elute the product
  7. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-74d3064174304848be92c8f3714a2df6
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

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