Chlorotrimethylsilane → HCID 135533268, compound

HRID 341914Notes

Reaction equation

HRID 341914 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) δ0.75 (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-13a8887c4040482f834da96e60adc5e7
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Reaction notes

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