Hydrochloric Acid → HCID 67365690, compound

HRID 81331Notes

Reaction equation

HRID 81331 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]([CH2:29][C@@H:30]([OH:35])[C@@H:31]([OH:34])[CH2:32][OH:33])[CH2:22][C@@H:23]([OH:28])[C@@H:24]([OH:27])[CH2:25][OH:26])=[CH:14][CH:13]=1)(C)(C)C.Cl>C(O)C>[OH:35][C@@H:30]([C@@H:31]([OH:34])[CH2:32][OH:33])[CH2:29][N:21]([CH2:22][C@@H:23]([OH:28])[C@@H:24]([OH:27])[CH2:25][OH:26])[CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67367671HCID 67367671, compound

Product 1

HCID 67365690HCID 67365690, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution containing the compound 18 (0.502 g, 0.972 mmol) in ethanol (10 mL) was slowly added concentrated hydrochloric acid (12N, 2 mL). The clear solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated under vacuum. The residue was taken into ethanol (3 mL) and the resulting solution was concentrated again under vacuum. The procedure was repeated two more times to ensure no aqueous solvent remained. The residue was chromatographed over silica gel, eluting with a mixture of concentrated ammonium hydroxide (0-10%), methane (0-30%), and methylene chloride (100-60%), to afford 0.396 g (98%) of the product 19 as a low melting white solid. [α]D25=+24.2° (c 0.265, MeOH). 1H NMR (300 MHz, DMSO-d6): δ 1.32-1.52 (m, 4H), 2.46-2.55 (m, 4H), 2.74-2.79 (m, 2H), 2.84-2.96 (m, 2H), 3.31-3.99 (m, 16H), 4.01 (t, J=5.9 Hz, 2H), 6.40 (br s, 2H), 6.82 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H). m/z (APCI)=417 [C20H36N2O7+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. concentrationthe resulting solution was concentrated again under vacuum
  3. customThe residue was chromatographed over silica gel
  4. washeluting with a mixture of concentrated ammonium hydroxide (0-10%), methane (0-30%), and methylene chloride (100-60%)

Sources & evidence

ORD record
ord-4e13e435ff3541f2bf06e2d2c56842b1
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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