Trifluoroacetic acid methylene chloride → HCID 90411411, compound

HRID 1427739Notes

Reaction equation

HRID 1427739 reaction equation
C(OC(=O)N[CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][N:37]=[N+:38]=[N-:39])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)(C)(C)C.C(Cl)Cl.[C:45]([OH:51])(C(F)(F)F)=[O:46]>>[N:37]([CH2:36][CH2:35][CH2:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][C:45]([OH:51])=[O:46])=[CH:25][CH:24]=2)=[O:40])=[CH:28][CH:29]=1)=[N+:38]=[N-:39]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131732354HCID 131732354, compound

Product 1

HCID 90411411HCID 90411411, compoundYield 97%

Procedure

tert-butyl-(2-(2-(2-(2-((4-(4-(3-azidopropoxy)benzoyl)phenyl)-amino)ethoxy)ethoxy)ethoxy)ethyl)-carbamate (1.75 g, 2.91 mmol) was dissolved in a solution of DCM:TFA (2:1, 12 ml) and left to stir for ca. 1 h. Upon completion, reaction was then concentrated under reduced pressure, co-evaporated with toluene, and left on oil pump for 5 hs to yield 1.52 g (97.0% yield) of (2-(2-(2-(2-((4-(4-(3-azidopropoxy)benzoyl)phenyl)-amino)ethoxy)ethoxy)ethoxy)ethyl)carboxylic acid as colorless oil.

Workup

  1. waitleft
  2. customUpon completion, reaction
  3. concentrationwas then concentrated under reduced pressure, co-evaporated with toluene
  4. waitleft on oil pump for 5 hs

Sources & evidence

ORD record
ord-3369d8aacc5d4881a556d66324250037
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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