Sodium Hydroxide → HCID 86700232, compound

HRID 879427Notes

Reaction equation

HRID 879427 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:29]=[CH:28][C:22]4[N:23]([CH3:27])[C:24]([CH3:26])=[N:25][C:21]=4[CH:20]=3)[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+]>CO.C1COCC1>[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:29]=[CH:28][C:22]4[N:23]([CH3:27])[C:24]([CH3:26])=[N:25][C:21]=4[CH:20]=3)[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86700233HCID 86700233, compound

Product 1

HCID 86700232HCID 86700232, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate in MeOH (2 mL) and THF (2 mL) was added a sodium hydroxide solution (2 M aqueous, 500 μL). The reaction mixture was stirred at 50° C. for 4 h. The mixture was purified using reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C29H29ClN3O3S: 534.2 (M+H+); Found: 534.2 (M+H+); 1H NMR (400 MHz, CD3OD): δ 8.38 (s, 1H), 8.23 (d, J=8.8 Hz, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.87 (s, 1H), 7.69 (m, 1H), 7.60 (m, 3H), 5.26 (s, 1H), 4.00 (s, 3H), 2.87 (s, 3H), 2.62 (s, 3H), 0.97 (s, 9H).

Workup

  1. customThe mixture was purified
  2. washeluting by 5-100% acetonitrile in H2O with 0.1% TFA
  3. customto give the product

Sources & evidence

ORD record
ord-d4c79bcfebb04ebe8e2cc554b5f22211
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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