Hydrochloric Acid → HCID 66818494, compound

HRID 1755044Notes

Reaction equation

HRID 1755044 reaction equation
CC(C)([O-])C.[K+].C[O:8][C:9](=[O:44])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][S:18]([N:21]2[CH2:42][CH2:41][C:24]3([N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][CH:32]([CH2:35][CH:36]=[C:37]([F:39])[F:38])[CH2:31][CH2:30]4)[NH:26][C:25]3=[O:40])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[C:12]([CH3:43])[CH:11]=1.Cl>C(O)(C)(C)C.O1CCCC1.COC(C)(C)C>[F:39][C:37]([F:38])=[CH:36][CH2:35][CH:32]1[CH2:33][CH2:34][CH:29]([C:27]2[NH:26][C:25](=[O:40])[C:24]3([CH2:41][CH2:42][N:21]([S:18]([CH2:17][CH2:16][C:13]4[CH:14]=[CH:15][C:10]([C:9]([OH:44])=[O:8])=[CH:11][C:12]=4[CH3:43])(=[O:20])=[O:19])[CH2:22][CH2:23]3)[N:28]=2)[CH2:30][CH2:31]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 66816920HCID 66816920, compound

Product 1

HCID 66818494HCID 66818494, compoundYield 110.2%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Potassium t-butoxide (15.6 mg) was added to a solution of 4-(2-{2-[4-(3,3-difluoro-allyl)-cyclohexyl]-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl}-ethyl)-3-methyl-benzoic acid methyl ester (25.6 mg, 46.4 μmol) in t-butanol (464 μL) and tetrahydrofuran (464 μL), and the mixture was stirred at room temperature for two days. The reaction mixture was diluted with tert-butyl methyl ether and then adjusted to pH 1 with 2 N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was then dried to give 4-(2-{2-[4-(3,3-difluoro-allyl)-cyclohexyl]-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl}-ethyl)-3-methyl-benzoic acid (27.5 mg, 91%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residue was then dried

Sources & evidence

ORD record
ord-978c905d79be4c00ab453e6b0f4fdb22
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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