Hydrochloric Acid → HCID 58554762, compound

HRID 449762Notes

Reaction equation

[OH-].[K+].C[O:4][C:5](=[O:36])[C@@H:6]([N:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:22])[C:13]1[CH:18]=[CH:17][C:16]([N:19]=[N+:20]=[N-:21])=[CH:15][CH:14]=1.CO.Cl>C1(C)C=CC=CC=1>[N:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([N:23]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:29]3[C:24]2=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:5]([OH:36])=[O:4])=[O:22])=[CH:18][CH:17]=1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 60 °C

Procedure

Methanolic KOH (0.075 g, 1.32 mmol) was added to a stirred solution of (S)-6-(4-azido-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 13 (0.200 g, 0.44 mmol) in a mixture (2:1) of methanol (6 mL) and toluene (3 mL) at room temperature. The reaction mixture was refluxed at 60° C. for 3.5 h. After cooling to 0° C., 1M HCl solution was added drop-wise for the acidification up to pH=3-4 and extracted with EtOAc (30 mL×2). The combined organic extract was washed with water (20 mL×2) and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure provided (S)-6-(4-azido-benzoylamino)-2-carbazol-9-yl-hexanoic acid 14 (0.170 g, 88%) as a yellow solid.

Workup

temperatureAfter cooling to 0° C.
extractionextracted with EtOAc (30 mL×2)
extractionThe combined organic extract
washwas washed with water (20 mL×2)
dry with materialdried over anhydrous Na2SO4
customRemoval of solvent under reduced pressure

Sources & evidence

ORD record: ord-de23bba45a4349dabe89ec3c3b97b1bd
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486534B2

Reaction notes

Loading…