Sodium Hydroxide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879407Notes

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:27]=[C:26]4[C:22]([C:23]([CH3:29])=[N:24][N:25]4[CH3:28])=[CH:21][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+]>C1COCC1.CCO>[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:27]=[C:26]4[C:22]([C:23]([CH3:29])=[N:24][N:25]4[CH3:28])=[CH:21][CH:20]=3)[S:18][C:14]=2[C:13]=1[C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a vial was dissolved (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (100 mg, 0.178 mmol) in THF (4 mL) and EtOH (2 mL). 1M NaOH (2 mL) was added, and the mixture was heated to 50° C. overnight. The reaction was cooled to 23° C., and filtered (0.45 micron teflon syringe filter). The filtrate was purified by reverse phase HPLC, eluting with 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+: calc'd for C29H29ClN3O3S: 534.1 (M+H+); Found: 534.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.04 (s, 1H), 7.77 (s, 1H), 7.70 (q, J=8.7 Hz, 3H), 7.57 (d, J=6.1 Hz, 3H), 5.25 (s, 1H), 3.98 (s, 3H), 2.59 (s, 3H), 2.51 (s, 3H), 0.97 (s, 9H).

Workup

temperatureThe reaction was cooled to 23° C.
filtrationfiltered
filtration(0.45 micron teflon syringe filter)
customThe filtrate was purified by reverse phase HPLC
washeluting with 5-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record: ord-c72705cb10da48638a63948256c8e931
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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