Trifluoroacetic acid methylene chloride → HCID 21886753, compound

HRID 723146Notes

Reaction equation

HRID 723146 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:43])[C:9]1[S:10][C:11]([S:41][CH3:42])=[C:12]([S:14]([C:17]2[CH:18]=[C:19]([C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=3[NH:30][C:31]([NH:33][CH2:34][CH2:35][C:36]3[N:37]=[N:38][NH:39][N:40]=3)=[O:32])[CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].C(Cl)Cl>>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[CH3:42][S:41][C:11]1[S:10][C:9]([C:8]([NH2:43])=[NH:7])=[CH:13][C:12]=1[S:14]([C:17]1[CH:18]=[C:19]([C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=2[NH:30][C:31]([NH:33][CH2:34][CH2:35][C:36]2[N:40]=[N:39][NH:38][N:37]=2)=[O:32])[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 145857614HCID 145857614, compound

Product 1

HCID 21886753HCID 21886753, compoundYield 46%

Procedure

A solution of {imino-[5-methylsulfanyl-4-(6′-methyl-2′-{3-[2-(2H-tetrazol-5-yl)-ethyl]-ureido}-biphenyl-3-sulfonyl)-thiophen-2-yl]-methyl}-carbamic acid tert-butyl ester (10 mg, 15.3 μmol) in TFA/DCM (2.0 mL, 1:1) was stirred at ambient temperature for 1.5 h. The reaction mixture was concentrated to dryness, and flash chromatographed on silica gel column, eluting with 10% MeOH/DCM containing 0.1% TFA to give the title compound (4.7 mg, 46% yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness, and flash
  2. customchromatographed on silica gel column
  3. washeluting with 10% MeOH/DCM containing 0.1% TFA

Sources & evidence

ORD record
ord-60f7ab27712e4786a7ed343d11e32ec2
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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