Palmitoyl chloride → HCID 136333583, compound

HRID 969763Notes

Reaction equation

HRID 969763 reaction equation
O.[C@@H:2]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.C(N(CC)CC)C.[C:28](Cl)(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.O.CN(C)C=O>[C:28]([C@@:2]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1)(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

8

Reactant 4

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 1354457052'-Deoxyguanosine monohydrate

Product 1

HCID 136333583HCID 136333583, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a 250 mL flask was added 2′-deoxyguanosine mono-hydrate (5.0 g, 17.5 mmol), triethylamine (3.13 ml, 22.4 mmol) and N,N-dimethyl-4-aminopyridine (0.046 g, 0.37 mmol). N,N-dimethylformamide (130 mL) was added via cannula with stirring and the flask was purged with argon gas. The slurry was allowed to cool 10 minutes in an ice/NaCl bath and palmitoyl chloride (6.3 mL, 20.6 mmol) was added dropwise. The mixture was allowed to stir while it slowly warmed to 25 degrees C. After 72 h, the mixture was poured with stirring into 400 mL of a 1:1 mixture of water and saturated aqueous sodium bicarbonate solution, which mixture had been warmed to about 60 degrees C. The resulting white solid was isolated by suction filtration, washed with water, and dried.

Workup

  1. customthe flask was purged with argon gas
  2. temperatureto cool 10 minutes in an ice/NaCl bath
  3. stirringto stir while it
  4. additionthe mixture was poured
  5. temperaturehad been warmed to about 60 degrees C
  6. customThe resulting white solid was isolated by suction filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e59b8618592f43a8badd0882574dd280
Source dataset
uspto-grants-2007_12
Patent number
US07307166B1

Reaction notes

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