Ethanol hydrochloride → HCID 86651788, compound

HRID 2359803Notes

Reaction equation

HRID 2359803 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)(=[O:31])=[O:30])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:20][CH:19]=2)[N:10]=1)(C)(C)[CH3:2].Cl.C(O)C>>[CH2:1]([O:5][C:6](=[O:45])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)(=[O:30])=[O:31])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:20][CH:19]=2)[N:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 86651779HCID 86651779, compound

Product 1

HCID 86651788HCID 86651788, compoundYield 84.1%

Procedure

To tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (120 mg, 0.184 mmol) obtained in Example 3-(a) was added a 6M hydrogen chloride/ethanol solution (1 ml), and the mixture was left at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and a saturated aqueous sodium hydrogencarbonate solution was added to the residue, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (81.0 mg) as a colorless oil. (Yield: 84%)

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-60e4a09dd7be466f82ca7be173a89181
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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