Hydrochloric Acid → HCID 71624889, compound

HRID 2422188Notes

Reaction equation

HRID 2422188 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 71624888HCID 71624888, compound

Product 1

HCID 71624889HCID 71624889, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of conc. hydrochloric acid (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 was taken up in ethyl acetate. Any undissolved residue was collected by filtration. The filtrate was subjected to flash column chromatography (eluent ethyl acetate:methanol 95:5). The solid residue and the product collected from the chromatography were pooled together to give the title compound (600 mg, 42% yield).

Workup

  1. customThe solvent was evaporated off
  2. filtrationAny undissolved residue was collected by filtration
  3. customThe solid residue and the product collected from the chromatography

Sources & evidence

ORD record
ord-1b07184cc5954381879bdac51c184d74
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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