Sulfuric Acid → HCID 67527849, compound

HRID 1840397Notes

Reaction equation

HRID 1840397 reaction equation
O1C2C=CC=CC=2N=C1.NC1C=CC=CC=1.C(OC(=O)[NH:23][C@@H:24]1[CH2:28][CH2:27][N:26]([S:29]([C:32]2[C:40]3[O:39]C(C(C)(C)C)=[N:37][C:36]=3[CH:35]=[CH:34][C:33]=2[Cl:45])(=[O:31])=[O:30])[CH2:25]1)(C)(C)C.OS(O)(=O)=O>O1CCOCC1.O>[NH2:37][C:36]1[C:40]([OH:39])=[C:32]([S:29]([N:26]2[CH2:27][CH2:28][C@@H:24]([NH2:23])[CH2:25]2)(=[O:31])=[O:30])[C:33]([Cl:45])=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 9228BenzoxazoleHCID 67527323HCID 67527323, compound

Product 1

HCID 67527849HCID 67527849, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Following the general procedure for the hydrolysis of the benzooxazole to the desired aniline outlined in example 51, [(R)-1-(2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (2.0 g, 4.31 mmol), water (3.6 mL), and H2SO4 (3.6 mL) in 1,4-dioxane (60 mL) were reacted to afford the title compound (1.2 g, 94%). LCMS m/z 292(M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-027d103ff7414ed5a638403eab2e1599
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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