Hydrochloric Acid → HCID 52939778, compound

HRID 1807581Notes

Reaction equation

HRID 1807581 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][CH2:22][C@H:23]4[NH:28][S:29]([CH2:32][C:33]([O:35]C)=[O:34])(=[O:31])=[O:30])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+].Cl>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][CH2:22][C@H:23]4[NH:28][S:29]([CH2:32][C:33]([OH:35])=[O:34])(=[O:30])=[O:31])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67200787HCID 67200787, compound

Product 1

HCID 52939778HCID 52939778, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Prepared using General Procedure 7: To a stirring solution of (R)-methyl 2-(N-(5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)sulfamoyl)acetate INT-14 (0.082 g, 0.16 mmol) in MeOH (1.5 mL) was added 6N NaOH (0.08 mL). The reaction was stirred at room temperature for 6 h. The crude reaction was diluted with water, acidified with 1N HCl and extracted with DCM and EA. The organic layer was dried over Na2SO4, concentrated, and isolated after preparative HPLC purification to give 0.057 g (72%) of (R)-2-(N-(5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)sulfamoyl)acetic acid 34. An analytically pure sample was prepared by preparative HPLC purification. LCMS-ESI (m/z) calculated for C24H26N4O6S: 496.5; found 520.1 [M+Na]+, tR=3.47 min.

Workup

  1. customPrepared
  2. customThe crude reaction
  3. extractionextracted with DCM and EA
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customisolated
  7. customafter preparative HPLC purification

Sources & evidence

ORD record
ord-3f786c087d954e0ca6e6b34b9f4c82a5
Source dataset
uspto-grants-2013_01
Patent number
US08357706B2

Reaction notes

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