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Pyridine → HCID 57741115, compound

HRID 1092433
Notes
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Reaction equation

HRID 1092433 reaction equation
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C@@H:20]([OH:21])[C@H](CO)[C@@H:18]([OH:24])[C@H:17]([OH:25])[C@H:16]2[OH:26])=[CH:11][C:10]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:5]([O:4][CH2:2][C@@H:1]1[C@@H:18]([OH:24])[C@H:17]([OH:25])[C@@H:16]([OH:26])[C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[C:10]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([CH2:34][CH3:35])=[CH:32][CH:33]=3)[CH:11]=2)[C@H:20]1[OH:21])(=[O:6])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 42622954HCID 42622954, compound

Product 1

HCID 57741115HCID 57741115, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

Ac2O (377 mg, 1.5 eq) 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) and DMAP (cat.) in CH2Cl2 (10 mL) at 0° C. followed by pyridine (292 mg, 1.5 eq), and the mixture was stirred overnight at rt. The reaction mixture was washed with 3N HCl, and the organic layer was combined, dried over Na2SO4, filtered, and the filtrate was evaporated to dryness. The residue was purified by preperative HPLC to give target compound (566 mg, white solid, yield of 50.4%). 1H-NMR (400 MHz, CD3OD): δ 7.32 (1H, d, J=8.4 Hz), 7.06-7.14 (6H, m), 4.37 (2H, ddd, J=2.0, 10.8, 16.8 Hz), 4.04 (2H, s), 3.57 (1H, t, J=10.8 Hz), 3.40-3.47 (1H, m), 2.49-2.60 (3H, m), 2.04 (3H, s), 1.60-1.66 (1H, m), 1.18 (3H, t, J=8.0 Hz); MS (ESI+): 449 [M+H]+, 466 [M+NH4]+, 897 [2M+H]+, (ESI−): 492 [M+HCOO]−, 941 [2M+HCOO]−.

Workup

  1. washThe reaction mixture was washed with 3N HCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by preperative HPLC
  6. customto give target compound (566 mg, white solid, yield of 50.4%)

Sources & evidence

ORD record
ord-3f9fbf09a3e54d60a677210f2d85d9f6
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129434B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes