Pivaloyl chloride → HCID 135986991, compound

HRID 1370004Notes

Reaction equation

HRID 1370004 reaction equation
CO[N:3](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:4]1[NH:5][C:6](=[O:20])[C:7]2[N:8]=[CH:9][N:10]([CH2:13][CH2:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17])[C:11]=2[N:12]=1.[C:40](Cl)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]>N1C=CC=CC=1>[C:40]([O:19][CH2:18][CH:15]([CH2:16][O:17][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:14][CH2:13][N:10]1[CH:9]=[N:8][C:7]2[C:6](=[O:20])[NH:5][C:4]([NH2:3])=[N:12][C:11]1=2)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 136341215HCID 136341215, 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 chloroform-methanol (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 (18H, s, 2×C(CH3)3), 1.81 (2H, q, J 6.8 Hz, 2′-H), 1.93 (1H, m, 3′-H), 4.0-4.1 (6H, m, 1′-H and 2×4′-H), 6.38 (2H, s, 2-NH2), 7.69 (1H, s, 8-H), and 10.58 (1H, 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 chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-0b093867595a4f098bd530a7656206ca
Source dataset
uspto-grants-2003_06
Patent number
US06579981B1

Reaction notes

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