Acetic Acid → HCID 68904902, compound

HRID 490052Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:30])[O:6][CH:7]1[CH:11]([OH:12])[CH:10]([CH2:13][OH:14])[O:9][CH:8]1[N:15]1[C:19]2[N:20]=[C:21]([N:24]=CN(C)C)[N:22]=[CH:23][C:18]=2[S:17][C:16]1=[O:29])([CH3:3])[CH3:2].CC(O)=O>CO>[CH:1]([O:4][C:5](=[O:30])[O:6][CH:7]1[CH:11]([OH:12])[CH:10]([CH2:13][OH:14])[O:9][CH:8]1[N:15]1[C:19]2[N:20]=[C:21]([NH2:24])[N:22]=[CH:23][C:18]=2[S:17][C:16]1=[O:29])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 35 °C

Procedure

Carbonic acid 2-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo [4,5-d]pyrimidin-3-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester isopropyl ester (15) (460 mg, 1.04 mmol) was dissolved in MeOH (5.0 mL) and HOAc (1.0 mL) was added. The reaction was warmed to 35° C. for 48 h, concentrated to a solid residue in vacuo, then subjected to flash chromatography (40-100% EtOAc-hexanes). The solids were triturated with a minimum of Et2O to yield 275 mg (69%) of 16 as a white powder: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (1H, s), 6.86 (2H, bs), 5.87 (1H, d, J=5.6 Hz), 5.68 (1H, dd, J1=4.5 Hz, J2=8.3 Hz), 5.46 (1H, d, J=7.0 Hz), 4.66 (1H, septet, J=6.2 Hz), 4.58 (1H, t, J=5.8 Hz), 4.33-4.37 (1H, m), 3.96-4.03 (1H, m), 3.62-3.72 (2H, m), 1.17 (3H, d, J=6.3 Hz), 1.12 (3H, d, J=6.2 Hz); [M]+ @ m/z 386.9.

Workup

concentrationconcentrated to a solid residue in vacuo
customThe solids were triturated with a minimum of Et2O

Sources & evidence

ORD record: ord-585f8657e094463d98b6f27af8ce0f6e
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528115B2

Reaction notes

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