Hydrochloric Acid → HCID 57741106, compound

HRID 1092434Notes

Reaction equation

HRID 1092434 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([OH:15])[C@H:13]([CH2:16][OH:17])[C@@H:12]([OH:18])[C@H:11]([OH:19])[C@H:10]2[OH:20])=[CH:5][C:4]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=1.[CH3:30][C:31]#N.[CH3:33]O>CC(C)=O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@H:14]3[O:15][C:31]([CH3:30])([CH3:33])[O:17][CH2:16][C@@H:13]3[C@@H:12]([OH:18])[C@H:11]([OH:19])[C@H:10]2[OH:20])=[CH:5][C:4]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6342AcetonitrileHCID 42622954HCID 42622954, compound

Product 1

HCID 57741106HCID 57741106, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1N HCl (5 mL) was added dropwised into the solution of (1R,2R,3S,4R,5R,6S)-4-(4-chloro-3-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraol (5, R=Et, 1 g, 2.46 mmol) in MeOH (80 mL) and acetone (20 mL), and stirred overnight, then the mixture was evaporated to dryness. The residue was purified by preparative HPLC to give the target compound (864 mg, white solid, yield of 75.3%). 1H-NMR (400 MHz, CD3COCD3): δ 7.26-7.29 (2H, m), 7.10-7.16 (5H, m), 3.74-4.21 (6H, m), 3.46-3.51 (1H, m), 3.35-3.37 (1H, m), 2.56-2.66 (3H, m), 1.72-1.75 (1H, m), 1.28 (3H, s), 1.18 (3H, t, J=7.6 Hz), 1.13 (3H, s); MS (ESI+): 447 [M+H]+, 488 [M+H+CH3CN]+, 910 [2M+NH4]+, 491 [M+HCOO]−, 937 [2M+HCOO]−.

Workup

  1. customthe mixture was evaporated to dryness
  2. customThe residue was purified by preparative HPLC
  3. customto give the target compound (864 mg, white solid, yield of 75.3%)

Sources & evidence

ORD record
ord-0645170dfe35410a8078a3691f3518ab
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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