Acetic Acid → HCID 68901568, compound

HRID 490054Notes

Reaction equation

HRID 490054 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:8]([N:22]2[C:26]3[N:27]=[C:28]([NH:31]C=O)[N:29]=[CH:30][C:25]=3[S:24][C:23]2=[O:34])[O:7]1)(=[O:3])[CH3:2].CC(O)=O>CO>[C:1]([O:4][CH2:5][CH:6]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:8]([N:22]2[C:26]3[N:27]=[C:28]([NH2:31])[N:29]=[CH:30][C:25]=3[S:24][C:23]2=[O:34])[O:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 76589389HCID 76589389, compound

Product 1

HCID 68901568HCID 68901568, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 3-acetoxy-5-(5-formylamino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-isopropoxycarbonyloxy-tetrahydro-furan-2-ylmethyl ester (58) (420 mg, 0.84 mmol) was dissolved in MeOH (8.4 mL), cat. HOAc, and heated to 85° C. for 2 days. The reaction mixture was reduced to an oil in vacuo then subjected to flash chromatography (10-80% EtOAc-hexanes) yielding 310 mg (78%) of 59 as a pure white solid: 1HNMR (400 MHz, DMSO-d6) δ 8.37 (1H, s), 6.88 (2H, bs), 5.91-5.98 (2H, m), 5.47 (1H, dd, J1=5.2 Hz, J2=8.3 Hz), 4.65 (1H, septet, J=6.2 Hz), 4.46-4.51 (1H, m), 4.28 (1H, dd, J1=4.2 Hz, J2=11.9 Hz), 4.18 (1H, dd, J1=7.8 Hz, J2=11.6 Hz), 2.11 (3H, s),2.00 (3H, s), 1.16 (3H, d, J=6.3 Hz), 1.12 (3H, d, J=6.2 Hz).

Sources & evidence

ORD record
ord-7884c0406c254f179a51f37743b4da6f
Source dataset
uspto-grants-2009_05
Patent number
US07528115B2

Reaction notes

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