TFA dichloromethane water → 1-Methyl-cyclopropanesulfonic acid (18-hydroxy-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carbonyl)-amide

HRID 390132Notes

Reaction equation

HRID 390132 reaction equation
C(OC[O:5][CH:6]1[CH2:24][CH:23]2[N:8]([C:9](=[O:45])[N:10](CC3C=CC(OC)=CC=3)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH:18]3[C:20]([C:26]([NH:28][S:29]([C:32]4([CH3:35])[CH2:34][CH2:33]4)(=[O:31])=[O:30])=[O:27])([NH:21][C:22]2=[O:25])[CH2:19]3)[CH2:7]1)C.ClCCl.FC(F)(F)C(O)=O.O>C(OCC)(=O)C.CO>[OH:5][CH:6]1[CH2:24][CH:23]2[N:8]([C:9](=[O:45])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH:18]3[C:20]([C:26]([NH:28][S:29]([C:32]4([CH3:35])[CH2:34][CH2:33]4)(=[O:31])=[O:30])=[O:27])([NH:21][C:22]2=[O:25])[CH2:19]3)[CH2:7]1

Participants

4

Reactant 2

HCID 18672661TFA dichloromethane waterHCID 722366171-Methyl-cyclopropanesulfonic acid [18-ethoxymethoxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carbonyl]-amide

Product 1

HCID 722366101-Methyl-cyclopropanesulfonic acid (18-hydroxy-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carbonyl)-amideYield 30%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The acetal compound 22a (0.301 g, 0.465 mmol) was deprotected using 2:1:0.1 dichloromethane/trifluoroacetic acid/H2O (6.2 ml) at rt for 4 h, then conc onto silica and flash chromatography using 9:1 ethyl acetate/methanol gave the product as a colorless foam (0.065 g, 30%). LR-MS: Calcd for C21H33N4O6S: 469. Found: 469 [M+H].

Workup

  1. customat rt
  2. customfor 4 h

Sources & evidence

ORD record
ord-052cd2f6fcf64e76bf20917afcbf29f5
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

Loading…