Hydrochloric Acid → HCID 58897168, compound

HRID 1365500Notes

Reaction equation

HRID 1365500 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([F:31])[CH:22]=2)([NH:14][S@@](C(C)(C)C)=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1.Cl>CO.O1CCOCC1.CCOC(C)=O>[NH2:14][C@:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)([C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:24]=[C:23]([F:31])[CH:22]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66814874HCID 66814874, compound

Product 1

HCID 58897168HCID 58897168, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-methyl 3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)-3-((R)-2-methylpropan-2-ylsulfinamido)propanoate (0.075 g, 0.16 mmol) was dissolved in MeOH (2 mL). At RT, 4.0M HCl in dioxane (2 mL) was added and the reaction mixture stirred for 30 min. The reaction mixture was diluted with EtOAc (50 mL), transferred to a separation funnel and washed with 1.0M NaOH (ca.20 mL). The organic portion was dried over anhydrous Na2SO4, decanted and concentrated yielding (S)-methyl 3-amino-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl)propanoate as a colorless oil, (0.062 g, crude quantitative yield). LCMS: 1.37 min [M+1] 377.1 (2 min gradient, MeOH/H2O 0.1% TFA).

Workup

  1. customtransferred to a separation funnel
  2. washwashed with 1.0M NaOH (ca.20 mL)
  3. dry with materialThe organic portion was dried over anhydrous Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b0a92b7428fb45368ff852129932aab8
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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