Hydrochloric Acid → HCID 21905257, compound

HRID 1247419Notes

Reaction equation

HRID 1247419 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:15]([C:18](=[O:29])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[O:16][CH3:17])[C:9]=1[F:30])(C)(C)C.Cl>O1CCOCC1>[NH2:7][C:8]1[C:9]([F:30])=[C:10]([CH:15]([O:16][CH3:17])[C:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)=[O:29])[C:11]([F:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69652530HCID 69652530, compound

Product 1

HCID 21905257HCID 21905257, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (RS)-{3-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2,4-difluoro-phenyl}-carbamic acid tert-butyl ester (514 mg) at rt in dioxane (10 ml) under an argon atmosphere was added 4 M HCl solution in dioxane (6 ml). Stirring at rt was then continued for 3 h. The light yellow solution was concentrated. The solid residue was suspended in EtOAc and washed with 1 N NaOH. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 2:3) to give (RS)-2-(3-amino-2,6-difluoro-phenyl)-N-(4-cyano-benzyl)-2-methoxy-acetamide (215 mg) as an off-white solid. MS 332.3 ([M+H]+)

Workup

  1. concentrationThe light yellow solution was concentrated
  2. washwashed with 1 N NaOH
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 2:3)

Sources & evidence

ORD record
ord-6c0251306fb3427b87ac05b34bccade6
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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