Methanol → HCID 136344604, compound

HRID 1644572Notes

Reaction equation

HRID 1644572 reaction equation
[OH:1][CH2:2][C@H:3]([CH2:16][CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:10](=[O:14])[NH:9][C:8]([NH2:15])=[N:7][C:6]1=2.[C:36](Cl)(=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53].CO.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.ClCCl>[C:36]([O:1][CH2:2][C@H:3]([CH2:16][CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:10](=[O:14])[NH:9][C:8]([NH2:15])=[N:7][C:6]1=2)(=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

7

Reactant 4

HCID 887MethanolHCID 8212Stearoyl chloride2×HCID 516892Sodium BicarbonateHCID 136344530(R)-9-[2-Hydroxymethyl 4-(t-butyldiphenylsilyloxy)butyl]guanine

Product 1

HCID 136344604HCID 136344604, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

(R)-9-[2-Hydroxymethyl 4-(t-butyldiphenylsilyloxy)butyl]guanine (2.31 g, 5 mmole) was coevaporated with dry pyridine twice and dissolved in pyridine (20 ml). To the solution was slowly added dropwise stearoyl chloride (1.86 ml, 5.5 mmole, technical grade) in dichloromethane (2 ml) at −5° C. The reaction was kept at the same temperature for 1 hr and then at 5° C. for 2 hr. The reaction was monitored by TLC. Additional stearoyl chloride (0.29 ml) at −5° C. was added due to incompletion of reaction. After 30 min at 5° C., methanol (3 ml) was added and the reaction mixture stirred for 20 min. It was then poured into aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The organic phase was dried and the product purified by silica gel column chromatography with stepwise increasing MeOH, eluting with 3.5% MeOH in CH2Cl2. (Yield 2.7 g).

Workup

  1. waitat 5° C. for 2 hr
  2. waitAfter 30 min at 5° C.
  3. extractionextracted with dichloromethane
  4. customThe organic phase was dried
  5. customthe product purified by silica gel column chromatography with stepwise increasing MeOH
  6. washeluting with 3.5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3bdcd624fbf24b7598aee98df8e18492
Source dataset
uspto-grants-2012_02
Patent number
US08124609B2

Reaction notes

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