Triacetoxyperiodinane → HCID 86712605, compound

HRID 2175305Notes

Reaction equation

HRID 2175305 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:45]=[C:44]([F:46])[C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[C:23]4[O:24][CH2:25][CH:26]([OH:43])[CH2:27][N:28]([C:29]([O:31][CH2:32][CH2:33][O:34][C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=5[CH3:42])=[O:30])[C:22]=4[CH:21]=[CH:20][CH:19]=3)[CH:15]=[N:14]2)=[C:10]([Cl:47])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6]([C:8]1[CH:45]=[C:44]([F:46])[C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[C:23]4[O:24][CH2:25][C:26](=[O:43])[CH2:27][N:28]([C:29]([O:31][CH2:32][CH2:33][O:34][C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=5[CH3:42])=[O:30])[C:22]=4[CH:21]=[CH:20][CH:19]=3)[CH:15]=[N:14]2)=[C:10]([Cl:47])[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86712606HCID 86712606, compound

Product 1

HCID 86712605HCID 86712605, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-(3-chloro-2-methylphenoxy)ethyl 9-(1-(4-(tert-butoxycarbonyl)-2-chloro-6-fluorobenzyl)-1H-pyrazol-4-yl)-3-hydroxy-3,4-dihydrobenzo[b][1,4]oxazepine-5(2H)-carboxylate (59 mg, 0.086 mmol) in DCM (5.0 mL) was added Dess-Martin periodinane (109 mg, 0.258 mmol). The reaction was stirred at room temperature for 2 d. The mixture was diluted with a solution of saturated sodium bicarbonate (15 mL) and extracted with DCM (20 mL). The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (58 mg, 92% yield) as white form. LCMS, [M+H]+=684.3. 1H NMR (400 MHz, CDCl3) δ 7.89-7.86 (m, 1H), 7.83 (d, J=6.8 Hz, 2H), 7.66 (dd, J=9.5, 1.5 Hz, 1H), 7.42 (dd, J=7.7, 1.5 Hz, 1H), 7.18 (br. s., 1H), 7.10-6.95 (m, 3H), 6.68 (d, J=7.3 Hz, 1H), 5.54 (d, J=1.5 Hz, 2H), 4.54 (s, 4H), 4.49 (s, 2H), 4.16 (br. s., 2H), 2.21 (br. s., 3H), 1.59 (s, 9H).

Workup

  1. extractionextracted with DCM (20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-90ee24ce752a487984d5664ef92a022d
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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