Trifluoroacetic acid → (R)-2-Amino-9-(2-stearoyloxymethyl-4-(L-valyloxy)butyl)purine

HRID 362611Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C@H:12]([CH2:30][O:31][C:32](=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:13][CH2:14][O:15][C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH:18]C(OC(C)(C)C)=O)=[CH:4][N:3]=1.FC(F)(F)C(O)=O>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C@H:12]([CH2:30][O:31][C:32](=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:13][CH2:14][O:15][C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH2:18])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 54149671HCID 54149671, compound

Product 1

HCID 54535483(R)-2-Amino-9-(2-stearoyloxymethyl-4-(L-valyloxy)butyl)purineYield 124.4%

Procedure

(R)-2-Amino-9-(2-Stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)purine (180 mg, 0.26 mmole) was treated with trifluoroacetic acid (5 ml) at 0° C. for 40 min. It was then evaporated in vacuo and coevaporated successively with toluene and methanol. The residue was freeze-dried overnight to give 195 mg of the desired product.

Workup

customIt was then evaporated in vacuo
customThe residue was freeze-dried overnight

Sources & evidence

ORD record: ord-2edfaba530cb4d359a9f2147c43894fe
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869493

Reaction notes

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