Trifluoroacetic acid → (2R)-(4'-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid

HRID 2187976Notes

Reaction equation

HRID 2187976 reaction equation
C([O:5][C:6](=[O:39])[C@H:7]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:8][CH2:9][CH2:10][N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[CH:28]=[CH:27][C:26]([S:23]([NH:22][C@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[C:6]([OH:39])=[O:5])(=[O:25])=[O:24])=[CH:31][CH:30]=2)=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15549670(2R)-(4'-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid t-butyl ester

Product 1

HCID 15549671(2R)-(4'-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acidYield 97%

Procedure

A solution of the title I compound, (2R)-(4′-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid t-butyl ester (0.96 g, 1.69 mmol) in TFA (10 mL, 130 mmol) is stirred at RT for 2.5 h. The solution is concentrated under reduced pressure to give a white solid which is triturated from 20 mL of diethyl ether, collected by filtration and dried to give 837 mg (97%) of (2R)-(4′-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid as a white solid: m.p. 179-181° C.; NMR(1:100 CD3OD/CDCl3) 1.65-1.86 (m, 4H), 3.63 (t, 3H, J=6.4), 3.93 (t, 3H, J=6.4), 7.39 (d, 2H, J=8.6), 7.47 (d, 2H, J=8.6), 7.60 (d, 2H, J=8.4), 7.65-7.68 (m, 2H), 7.76-7.79 (m, 2H), 7.86 (d, 2H, J=8.4); IR 1772, 1708, 1340, 1153; ESI-MS 511 (M−1), 513 (M++1).

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. customto give a white solid which
  3. customis triturated from 20 mL of diethyl ether
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-bb63dc6b1efd48da8fecd3699e07f016
Source dataset
uspto-grants-2002_06
Patent number
US06410580B1

Reaction notes

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