Hydrochloric Acid → HCID 70213943, compound

HRID 383139Notes

Reaction equation

HRID 383139 reaction equation
[CH3:1][O:2][C:3](=[O:46])[C@H:4]([CH2:42][CH2:43][S:44][CH3:45])[N:5](C(OC(C)(C)C)=O)[C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([NH:17][CH:18]([CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH3:19])[S:14][CH2:15][CH3:16])=[CH:9][C:8]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33].Cl>O1CCOCC1>[CH2:15]([S:14][CH:13]([NH:17][CH:18]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH3:19])[C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:46])[CH2:42][CH2:43][S:44][CH3:45])=[O:34])=[C:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH:9]=1)[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70213952HCID 70213952, compound

Product 1

HCID 70213943HCID 70213943, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-N-[4-(1-ethylsulfenyl-3-cyclohexylprop-2-ylaminomethyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester (200 mg) in dioxane (1 mL) chilled to its melting point, was added HCl (0.75 mL, 4M in dioxane). After 1 h, the reaction was quenched with excess aqueous sodium bicarbonate, and extracted into dichloromethane. The solution was concentrated, and the residue was purified by silica gel chromatography eluting with 5% methanol/dichloromethane to afford the title compound as a colorless oil (72 mg, 42%). MS (APCI(+)) 587 (M+H)+. MS (APCI(−)) 621 (M+CI)−.

Workup

  1. customthe reaction was quenched with excess aqueous sodium bicarbonate
  2. extractionextracted into dichloromethane
  3. concentrationThe solution was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-11c8545819e74c71b7b473e706230d1a
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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