Hydrochloric Acid → 4-(6-((S)-tert-butoxy(carboxy)methyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-ylamino)-3-(1-methyl-1H-indazol-5-yl)butanoic acid

HRID 510319Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (2S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(4-(1-methyl-1H-indazol-5-yl)-2-oxopyrrolidin-1-yl)benzo[d]thiazol-6-yl)acetate (5 mg) in THF/MeOH (0.5 mL/0.5 mL) was added sodium hydroxide solution (1.0 N, 0.5 mL). The mixture was stirred at 25° C. for 2 hours and heated at 50° C. for 16 hours. The mixture was cooled and neutralized with 0.1 N hydrochloric acid until pH=5. The reaction mixture was freeze-dried and used for next step without further purification. LCMS-ESI+: calc'd for C32H33ClN4O5S: 621.2 (M+H+); Found: 621.2 (M+H+).

Workup

temperatureheated at 50° C. for 16 hours
temperatureThe mixture was cooled
customThe reaction mixture was freeze-dried
customused for next step without further purification

Sources & evidence

ORD record: ord-7a4d3f4854d748bd83d38d6d80b749b1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096586B2

Reaction notes

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