Trifluoroacetic acid methylene chloride → HCID 21886439, compound

HRID 723144Notes

Reaction equation

HRID 723144 reaction equation
C(OC(=O)[NH:7][C:8](=[NH:64])[C:9]1[S:10][C:11]([S:62][CH3:63])=[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][CH2:36][CH2:37][C:38]3[N:39]=[N:40][N:41](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:42]=3)=[O:32])[CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C.[C:66]([OH:72])([C:68]([F:71])([F:70])[F:69])=[O:67].C(Cl)Cl>>[F:69][C:68]([F:71])([F:70])[C:66]([OH:72])=[O:67].[CH3:63][S:62][C:11]1[S:10][C:9]([C:8]([NH2:64])=[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][CH2:36][CH2:37][C:38]2[N:39]=[N:40][NH:41][N:42]=2)=[O:32])[CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 145857654HCID 145857654, compound

Product 1

HCID 21886439HCID 21886439, compoundYield 45%

Procedure

A solution of {imino-[5-methylsulfanyl-4-(6′-methyl-2′-{3-[4-(2-trityl-2H-tetrazol-5-yl)-butyl]-ureido}-biphenyl-3-sulfonyl)-thiophen-2-yl]-methyl}-carbamic acid tert-butyl ester (15 mg, 16 μmol) in TFA/DCM (1:1, 2.0 mL) was stirred at ambient temperature for 1 h. The mixture was concentrated, and flash chromatographed on silica gel column, eluting with MeOH/DCM (3 to 7.5% containing 0.1% TFA) to give the title compound (5 mg, 45% yield) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customflash chromatographed on silica gel column
  3. washeluting with MeOH/DCM (3 to 7.5% containing 0.1% TFA)

Sources & evidence

ORD record
ord-03b7af301b2443e9bbabf140c78c79b3
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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