Sodium Hydroxide → HCID 86700286, compound

HRID 879471Notes

Reaction equation

HRID 879471 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[N:23]([CH3:29])[CH2:22]4)[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[N:23]([CH3:29])[CH2:22]4)[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86700284HCID 86700284, compound

Product 1

HCID 86700286HCID 86700286, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-methyl-1-oxoisoindolin-5-yl)benzo[d]thiazol-6-yl)acetate (36 mg, 0.064 mmol) dissolved in THF/MeOH (1.25 mL/1.25 mL) and 2N NaOH (0.160 mL) was heated at 50° C. for 2 h and the crude was purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the title compound. LCMS-ESI+: calc'd for C29H27ClN2O4S: 535.1 (M+H+); found: 535.2 (M+H+). 1H NMR (400 MHz, DMSO-d6): δ 8.22 (s, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.87 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.65-7.51 (m, 4H), 5.03 (s, 1H), 4.46 (s, 2H), 3.03 (s, 3H), 2.48 (s, 3H), 0.83 (s, 9H).

Workup

  1. customthe crude was purified by reverse phase HPLC
  2. washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record
ord-4aedc6d6078e4239bfa5f503ea23ee2f
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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