Hydrochloric Acid → HCID 71624889, compound

HRID 415354Notes

Reaction equation

Cl.O.[OH:3][CH2:4][C@H:5]([NH:10][C:11]1[C:12]2[S:40][C:39]([O:41]C)=[N:38][C:13]=2[N:14]=[C:15]([S:17][S:18][C:19]2[N:20]=[C:21]([NH:30][C@H:31]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:32][OH:33])[C:22]3[S:27][C:26]([O:28]C)=[N:25][C:23]=3[N:24]=2)[N:16]=1)[CH2:6][CH:7]([CH3:9])[CH3:8]>O1CCOCC1>[OH:3][CH2:4][C@H:5]([NH:10][C:11]1[C:12]2[S:40][C:39](=[O:41])[NH:38][C:13]=2[N:14]=[C:15]([S:17][S:18][C:19]2[N:20]=[C:21]([NH:30][C@@H:31]([CH2:32][OH:33])[CH2:34][CH:35]([CH3:36])[CH3:37])[C:22]3[S:27][C:26](=[O:28])[NH:25][C:23]=3[N:24]=2)[N:16]=1)[CH2:6][CH:7]([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of conc. HCl (20 mL) and water (20 mL) was added to a solution of (2R)-2-{5-[7-((1R)-1-hydroxymethyl-3-methyl-butylamino)-2-methoxy-thiazolo[4,5-d]pyrimidin-5-yldisulfanyl]-2-methoxy-thiazolo[4,5-d]pyrimidin-7-ylamino}-4-methyl-pentan-1-ol (1.5 g, 2.4 mmol) in 1,4-dioxane (20 mL). The solution was then stirred at 45° C. for 18 h. The solvent was evaporated off and the residue taken up in EtOAc (undissolved residue was filtered off and was found to be pure by LCMS). The solution was subjected to flash chromatography (MeOH:EtOAc 5:95). The two samples were pooled together to give the title compound (600 mg, 42% yield).

Workup

customThe solvent was evaporated off

Sources & evidence

ORD record: ord-6e2b918542b94c37b12a48b433c3cb63
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088780B2

Reaction notes

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