9-Fluorenylmethyl chloroformate → HCID 86633937, compound

HRID 1041121Notes

Reaction equation

HRID 1041121 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:11])=[O:10].Cl[C:14]([O:16][CH2:17][CH:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15]>>[CH:29]1[C:30]2[CH:18]([CH2:17][O:16][C:14]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=3[S:9]([OH:12])(=[O:11])=[O:10])=[O:15])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 129043662-Amino-5-fluorobenzenesulfonic acid

Product 1

HCID 86633937HCID 86633937, compound

Procedure

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-fluoro-benzenesulfonic acid was prepared from 2-Amino-5-fluoro-benzenesulfonic acid (5.0 g, 0.026 mol) (Suter, C. M.; Weston, A. W., J. Amer. Chem. Soc., 1940, 62, 604-606) and 9-Fluorenylmethyl chloroformate (7.4 g, 0.029 mol) in an analogous manner to Example 820a. Product isolated as a white solid (8.08 g, 74%). 1HNMR (400 MHz, DMF-d7, δ, ppm): 10.25 (br s, 1H), 8.20-8.00 (m, 1H), 7.95 (d, 2H, J=7.3 Hz), 7.77 (d, 2H, J=7.3 Hz), 7.54 (dd, 1H, J=8.8 and 3.0 Hz), 7.45 (t, 2H, J=7.3 Hz), 7.38 (t, 2H, J=7.3 Hz), 7.21-7.12 (m, 1H), 4.70-4.10 (m, 4H).

Sources & evidence

ORD record
ord-c30f225329ba4b2faf10460d09920928
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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