Hydrochloric Acid → 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 390131Notes

Reaction equation

HRID 390131 reaction equation
C(OC[O:5][CH:6]1[CH2:24][CH:23]2[N:8]([C:9](=[O:44])[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]([CH:32]4[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.Cl.C(=O)([O-])O.[Na+]>C1COCC1.CO>[OH:5][CH:6]1[CH2:24][CH:23]2[N:8]([C:9](=[O:44])[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]([CH:32]4[CH2:33][CH2:34]4)(=[O:31])=[O:30])=[O:27])([NH:21][C:22]2=[O:25])[CH2:19]3)[CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 72236615Cyclopropanesulfonic 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 72236613Cyclopropanesulfonic acid (18-hydroxy-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carbonyl)-amideYield 73.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of the acetal 21j (0.038 g, 0.06 mmol) in 1:1:1 THF-methanol-2 M aq. hydrochloric acid (1.5 ml) was stirred at rt for 30 min, then additional conc. hydrochloric acid (0.1 ml) was added and then stirred at rt overnight. The reaction mixture was then neutralized using aq. saturated sodium hydrogen carbonate, then concentrated onto silica. Flash chromatography of the residue using 9:1 ethyl acetate methanol gave a colorless foam (0.020 g, 73%). LR-MS: Calcd for C20H29N4O6S: 453. Found: 453 [M−H].

Workup

  1. concentrationconcentrated onto silica

Sources & evidence

ORD record
ord-a7d7c68ce852464b90cf7d19d89732de
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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