Isopropanol → HCID 68563172, compound

HRID 19476Notes

Reaction equation

HRID 19476 reaction equation
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:33])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2].[CH:34]1[CH:39]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:35]=1.C(O)(C)C.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]([NH:4][C:5]1[N:6]=[C:7]([O:33][CH:34]([CH3:39])[CH3:35])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355085035-Acetylamino-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidine-2,7-dione

Product 1

HCID 68563172HCID 68563172, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 16 (650 mg, 1.34 mmol) and Argonaut PS-triphenylphosphine resin (4.02 mmol, 1.86 g) were placed under a dry nitrogen atmosphere in a flame-dried flask, and then dry THF (20 ml) was added. The flask was then cooled to 0° C. in an ice bath. Isopropanol (IPA) (0.20 ml, 2.68 mmol) was added followed by the dropwise addition of diethyl azodicarboxylate (DEAD) (0.366 ml, 2.0 mmol). The flask was removed from the ice bath and allowed to warm to ambient temperature. The reaction mixture was monitored for the disappearance of compound 16 by TLC. Upon consumption of 16, the solid supported material was filtered off. The crude reaction mixture was purified by flash chromatography using a 15 to 60% gradient of ethyl acetate in chloroform. Removal of the solvent afforded 460 mg (64.9%) of 27 as a white foam: MS (+)-ES [M+H]+ m/z 527. Rf=0.7 (75% Ethyl acetate -CHCl3).

Workup

  1. customThe flask was removed from the ice bath
  2. temperatureto warm to ambient temperature
  3. customUpon consumption of 16
  4. filtrationwas filtered off
  5. customThe crude reaction mixture
  6. customwas purified by flash chromatography
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-7582a907294a47d9a98db9405e9b7012
Source dataset
uspto-grants-2010_06
Patent number
US07745415B2

Reaction notes

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