Hydrochloric Acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid

HRID 879627Notes

Reaction equation

HRID 879627 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[CH:36][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[CH:36][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:39]1[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86700436(S)-2-tert-butoxy-2-(2-(3-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Product 1

HCID 86700437(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(piperazin-1-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-2-tert-butoxy-2-(2-(3-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid (from above) in 1,4-dioxane (5 mL) was added 4M HCl in 1,4-dioxane (1 mL, 4 mmol). The reaction was stirred at rt for 6 h. A saturated solution of NaHCO3 (10 mL) was added carefully. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo and used without further purification. LCMS-ESI+: calc'd for C30H33ClN3O3S: 550.2 (M+H+); Found: 550.2 (M+H+).

Workup

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customused without further purification

Sources & evidence

ORD record
ord-ce6e1d6fd88c4934bafe5f88c1f513c9
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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