Hydrochloric Acid → 4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)methyl)benzoic acid

HRID 1925188Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33](C3CC(=O)N(O)C3=O)=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.Cl>O1CCOCC1>[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([NH:1][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=3)=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To 4-aminomethyl-benzoic acid (10.6 g, 70.1 mmol) in dioxane (130 mL) was added 9% aqueous Na2CO3 (150 mL) followed by 9-fluorenylmethyloxycarbonyl-N-hydroxysuccinimide (26 g, 77 mmol). The solution was heated to 40° C. for 12 h and then cooled to room temperature. The reaction was acidified with 1 M HCl (500 mL), and extracted with ether (300 mL) to obtain acid S23 as a fluffy white solid (25.9 g, 69.4 mmol, 99%). 1H NMR (500 MHz, d6-DMSO): δ 12.85 (broad s, 1H), 7.90 (m, 4H), 7.70 (m, 2H), 7.39 (m, 2H), 7.31 (m, 4H), 4.37 (d, 2H, J=6.8 Hz), 4.24 (d, 2H, J=5.8 Hz), 4.23 (t, 1H, J=6.8 Hz). APCI/MS: 372 (M+H+).

Workup

temperaturecooled to room temperature
extractionextracted with ether (300 mL)

Sources & evidence

ORD record: ord-e28eb4aad354416cad5fd630f6e77115
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178579B2

Reaction notes

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