Ethyl Acetate → (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

HRID 879626Notes

Reaction equation

HRID 879626 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:38]([CH3:39])=[CH:37][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]4)[CH:21]=[CH:22][CH:23]=3)[S:17][C:13]=2[C:12]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:11]1[C:38]([CH3:39])=[CH:37][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N:24]4[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]4)[CH:19]=3)[S:17][C:13]=2[C:12]=1[C:40]1[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86700435(S)-tert-butyl 4-(3-(6-(1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-tert-butyl 4-(3-(6-(1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate (from above) in THF (4 mL) and methanol (4 mL) was added sodium hydroxide solution (1.0 mL, 2 mmol, 2 M aqueous solution). The mixture was stirred at 60° C. for 18 h. A saturated solution of NH4Cl (20 mL) and EtOAc (15 mL) were added. 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 C35H41ClN3O5S: 650.2 (M+H+); Found: 650.2 (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-8d83b20bb8a14bb781c4638cf9fc058b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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