Sodium Hydroxide → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid

HRID 602754Notes

Reaction equation

C[O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)[CH3:5].[OH-].[Na+].[NH4+].[Cl-]>C1COCC1.CO>[C:23]1([S:20]([C:4]([CH:6]2[CH2:18][CH2:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=4)[NH:9][C:8]=3[CH2:7]2)([CH3:5])[C:3]([OH:29])=[O:2])(=[O:22])=[O:21])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 50 mg (0.115 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester (example 3) in 4 mL of THF/MeOH 1:1, 0.29 mL of 2M NaOH (0.58 mmol, 5 eq) were added. The reaction mixture was stirred at 60° C. for 3 hours, acidified to pH=6 with aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with CH2Cl2/MeOH 3:1 yielded 40 mg (82%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid as a white solid, MS: 435 (MNH4+).

Workup

extractionextracted with EtOAc
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-a28de8c8657e47438319bd617ecfbfb6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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