Hydrochloric Acid → HCID 69950636, compound

HRID 366758Notes

Reaction equation

HRID 366758 reaction equation
[F:1][C:2]1[C:3]([C:20]#[C:21][C@@H:22]([NH:26][CH3:27])[C@H:23]([OH:25])[CH3:24])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19].Cl.CO.C(Cl)[Cl:32]>O1CCOCC1>[ClH:32].[F:1][C:2]1[C:3]([C:20]#[C:21][C@@H:22]([NH:26][CH3:27])[C@H:23]([OH:25])[CH3:24])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15907933(Z)-1,3-Dihydro-5-fluoro-4-[(3R,4R)-4-hydroxy-3-methylamino-1-pentynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-oneHCID 21226129Dichloromethane methanol

Product 1

HCID 69950636HCID 69950636, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (Z)-1,3-dihydro-5-fluoro-4-[(3R,4R)-4-hydroxy-3-methylamino-1-pentynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (35 mg, 0.07 mmol) (Example 117C) in dioxane (5 mL) was treated with aqueous HCl under vigorous stirring. (Z)-1,3-Dihydro-5-fluoro-4-[(3R,4R)-4-hydroxy-3-methylamino-1-pentynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one hydrochloride salt was obtained upon lyophilization and precipitation out of a (1:3, V/V) mixture of MeOH/CH2Cl2 with excess of hexanes. (Yield 32 mg, 83%).

Sources & evidence

ORD record
ord-dab14ccc4cae4c0898853ec924241fce
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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