Chloroform trifluoroacetic acid → [3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-2,6-dimethyl-biphenyl-4-yloxy]-acetic acid trifluoroacetate

HRID 2216143Notes

Reaction equation

HRID 2216143 reaction equation
C(Cl)(Cl)Cl.[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].C([O:16][C:17](=[O:54])[CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([C:36]3[CH:40]=[C:39]([C:41]([NH:43]C(OC(C)(C)C)=O)=[NH:42])[S:38][C:37]=3[S:51][CH3:52])(=[O:35])=[O:34])[CH:28]=2)=[C:22]([CH3:53])[CH:21]=1)(C)(C)C>>[F:5][C:6]([F:11])([F:10])[C:7]([OH:9])=[O:8].[C:41]([C:39]1[S:38][C:37]([S:51][CH3:52])=[C:36]([S:33]([C:29]2[CH:28]=[C:27]([C:23]3[C:24]([CH3:26])=[CH:25][C:20]([O:19][CH2:18][C:17]([OH:54])=[O:16])=[CH:21][C:22]=3[CH3:53])[CH:32]=[CH:31][CH:30]=2)(=[O:35])=[O:34])[CH:40]=1)(=[NH:42])[NH2:43]

Participants

3

Reactant 2

HCID 19978452Chloroform trifluoroacetic acidHCID 145857690tert-butyl 2-[3,5-dimethyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenoxy]acetate

Product 1

HCID 69586710[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-2,6-dimethyl-biphenyl-4-yloxy]-acetic acid trifluoroacetateYield 75%

Procedure

A solution of dichloromethane/trifluoroacetic acid (1/1) [2 mL] was added to {3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-2,6-dimethyl-biphenyl-4-yloxy}-acetic acid tert-butyl ester (0.020 g, 0.030 mmol) [example 215, step a] at room temperature and stirred for 1 hour. The reaction mixture was evaporated and purified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to give the title compound (0.011 g, 75%) as a solid. 1H-NMR (MeOD): δ 8.36 (s, 1H), 8.01 (md, 1H, J=7.6 Hz), 7.81 (m, 1H), 7.72 (m, 1H), 7.51 (d, 1H, J=7.6 Hz), 7.26 (d, 1H, J=8.0 Hz), 6.74 (s, 2H), 4.67 (s, 2H), 2.73 (s, 3H), 1.96 (s, 6H). ESI-MS (m/z): Calcd. for C22H22N2O5S3: 490.07; found: 491.2.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified via reverse-phase HPLC [acetonitrile/water (0.01% TFA)]

Sources & evidence

ORD record
ord-23c94747652943e3a301d08bc0215443
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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