Trifluoroacetic acid methylene chloride → (S)-3-methyl-2-{4'-[(5-chloro-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid

HRID 29447Notes

Reaction equation

HRID 29447 reaction equation
C([O:5][C:6](=[O:40])[C@@H:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[S:31][C:32]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:33]=4[N:34]=3)=[O:29])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH3:9][CH:8]([CH3:10])[C@H:7]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]3[S:31][C:32]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:33]=4[N:34]=3)=[O:29])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)(=[O:14])=[O:13])[C:6]([OH:40])=[O:5]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68713740(S)-3-methyl-2-{4'-[(5-chloro-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester

Product 1

HCID 11284178(S)-3-methyl-2-{4'-[(5-chloro-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acidYield 386.1%

Procedure

To (S)-3-methyl-2-{4′-[(5-chloro-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid tert-butyl ester (30 mg) was added 3 mL of TFA/CH2Cl2 (1:1). The solution was stirred at room temperature for 3 h. The solvents were removed under vacuum and the residue was triturated with ether. Filtration gave 105 mg of (S)-3-methyl-2-{4′-[(5-chloro-benzothiazole-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.79-0.88 (m, 6 H) 1.85-2.07 (m, 1 H) 3.56 (dd, 1 H) 7.70 (dd, 1 H) 7.76-7.94 (m, 6 H) 8.03-8.12 (m, 3 H) 8.26 (d, 1 H) 8.35 (d, 1 H) 11.36-11.40 (m, 1 H).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was triturated with ether
  3. filtrationFiltration

Sources & evidence

ORD record
ord-f2f2f0a1ea8c48bc86c13c43803821b9
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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