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

HRID 651324Notes

Reaction equation

HRID 651324 reaction equation
C([O:20][NH:21][C:22](=[O:55])[C@H:23]([NH:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)(=[O:41])=[O:40])[CH2:24][CH2:25][CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[OH:20][NH:21][C:22](=[O:55])[C@H:23]([NH:38][S:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=2)=[CH:44][CH:43]=1)(=[O:40])=[O:41])[CH2:24][CH2:25][CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 54536000(2R)-(4'-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid O-tritylhydroxyamide

Product 1

HCID 12049518(2R)-(4'-Chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid hydroxyamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title A compound, (2R)-(4′-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid O-tritylhydroxyamide (288 mg, 0.374 mmol) in 3 mL of dichloromethane is treated sequentially with triethylsilane (0.119 mL, 0.745 mmol) and trifluoroacetic acid (0.225 mL, 2.92 mmol) at 0° C. After 10 min, the solution is concentrated at 0° C. in a stream of nitrogen, and the residue is triturated from 5 mL of diethyl ether. The product is collected by vacuum filtration and dried to give 162.3 mg (82%) of (2R)-(4′-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid hydroxyamide as a white solid: m.p. 204-206° C. (dec); NMR(DMSO-d6) 1.24-1.33 (br m, 1H), 1.37-1.50 (br m, 3H), 3.39-3.47 (m, 2H), 3.52-3.62 (m, 1H), 7.53 (d, 2H, J=8.3), 7.70 (d, 2H, J=8.3), 7.80 (br s, 8H), 8.12 (d, 1H, J=8.5), 8.82 (br s, 1H), 10.56 (s, 1H); IR 1772, 1341, 1159; ESI-MS 528 (M++1).

Workup

  1. concentrationthe solution is concentrated at 0° C. in a stream of nitrogen
  2. customthe residue is triturated from 5 mL of diethyl ether
  3. filtrationThe product is collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-ea8d63ac626046dc964c436b469b0ed5
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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