Chlorotrimethylsilane → HCID 135533268, compound

HRID 368708Notes

Reaction equation

HRID 368708 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 an 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. temperaturecooled in an ice bath
  2. stirringThe solution was stirred for 4 hours during which it
  3. temperatureThe solution was cooled
  4. stirringthe solution was stirred for an additional 30 mins
  5. customthe solution evaporated an vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washto elute the product
  8. customProduct-containing fractions were evaporated

Sources & evidence

ORD record
ord-159f61df8017474e98530dc0525a2e7d
Source dataset
uspto-grants-2000_10
Patent number
US06133438

Reaction notes

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