Pivaloyl chloride → HCID 135986991, compound

HRID 1461522Notes

Reaction equation

HRID 1461522 reaction equation
N#N.CO[N:5](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]1[NH:7][C:8](=[O:22])[C:9]2[N:10]=[CH:11][N:12]([CH2:15][CH2:16][CH:17]([CH2:20][OH:21])[CH2:18][OH:19])[C:13]=2[N:14]=1.[C:42](Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]>N1C=CC=CC=1>[C:42]([O:21][CH2:20][CH:17]([CH2:18][O:19][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:16][CH2:15][N:12]1[CH:11]=[N:10][C:9]2[C:8](=[O:22])[NH:7][C:6]([NH2:5])=[N:14][C:13]1=2)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 136341214HCID 136341214, compound

Product 1

HCID 135986991HCID 135986991, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N2 -monomethoxytrityl-9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (0.47 g, 0.9 mmol) in pyridine (4.5 ml) was added pivalyl chloride (0.55 ml, 4.5 mmol) and the solution was stirred for 45 minutes. The mixture was precipitated in water (45 ml) and the resulting precipitate was stirred in 80% acetic acid (10 ml) at 80° for 20 minutes. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with chloroformmethanol (10:1) to afford 9-(4-pivalyloxy-3-pivalyloxymethylbut-1-yl)guanine (0.22 g, 58%), m.p. 225°-237° C.; νmax (KBr) 3430, 2980, 1730, 1690, and 1620 cm-1 ; δH [(CD3)2SO] 1.11 (18 H, s, 2×C(CH3)3), 1.81 (2 H, q, J 6.8 Hz, 2'-H), 1.93 (1 H, m, 3'-H), 4.0-4.1 (6 H, m, 1'-H and 2×4'-H), 6.38 (2 H, s, 2-NH2), 7.69 (1 H, s, 8-H), and 10.58 (1 H, br.s, 1-H); (Found: C, 56.58; H, 7.26; N, 16.14%; C20H31N5O5 requires: C, 56.99; H, 7.41; N, 16.62%).

Workup

  1. customThe mixture was precipitated in water (45 ml)
  2. stirringthe resulting precipitate was stirred in 80% acetic acid (10 ml) at 80° for 20 minutes
  3. customThe solvent was removed
  4. customthe residue was purified by column chromatography on silica gel eluting with chloroformmethanol (10:1)

Sources & evidence

ORD record
ord-7d10c93f064049e0b51ebff19b0d0741
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

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