Trifluoroacetic acid → Trifluoroacetate

HRID 634986Notes

Reaction equation

HRID 634986 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([NH:15][C@H:16]([C:20]([O:22][CH2:23][C@H:24]([CH2:37][CH2:38][O:39][C:40](=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:25][N:26]1[CH:34]=[N:33][C:32]2[C:31](=[O:35])[NH:30][C:29]([NH2:36])=[N:28][C:27]1=2)=[O:21])[CH:17]([CH3:19])[CH3:18])(OC(C)(C)C)=O>>[NH2:15][C@H:16]([C:20]([O:22][CH2:23][C@H:24]([CH2:37][CH2:38][O:39][C:40](=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:25][N:26]1[CH:34]=[N:33][C:32]2[C:31](=[O:35])[NH:30][C:29]([NH2:36])=[N:28][C:27]1=2)=[O:21])[CH:17]([CH3:19])[CH3:18].[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 135829460(R)-9-[2-(N-Boc-L-valyloxymethyl)4-(stearoyloxy)butyl]guanine

Product 2

HCID 84468TrifluoroacetateHCID 135423395(R)-9-[2(L-Valyloxymethyl)-4-(stearoyloxy)butyl]guanine

Procedure

Chilled trifluoroacetic acid (2.0 g) was added to (R)-9-[2-(N-Boc-L-valyloxymethyl)-4-(stearoyloxy)butyl]guanine (180 mg; 0.25 mmol) and the solution kept at room temperature for 1 h, evaporated to a small volume, and lyophilized repeatedly with dioxane until a white amorphous powder was obtained. The yield of title compound, obtained as the trifluoracetate salt, was quantitative.

Workup

  1. customevaporated to a small volume
  2. customwas obtained

Sources & evidence

ORD record
ord-18725cb90fe542a0bc1db4b407059fd3
Source dataset
uspto-grants-2001_02
Patent number
US06184376B2

Reaction notes

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