Peracetic Acid → HCID 117642231, compound

HRID 1499313Notes

Reaction equation

HRID 1499313 reaction equation
C(OO)(=[O:3])C.[C:6]([O:9][C@@H:10]1[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:14]([O:20][C:21](=[O:23])[CH3:22])[C@@H:13]([S:24][CH3:25])[O:12][C@H:11]1[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:36][CH:35]=2)[CH:27]=1)(=[O:8])[CH3:7]>CC(O)=O.CC#N>[C:6]([O:9][C@@H:10]1[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:14]([O:20][C:21](=[O:23])[CH3:22])[C@@H:13]([S@:24]([CH3:25])=[O:3])[O:12][C@H:11]1[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:38][CH:39]=2)[CH:27]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 90177037HCID 90177037, compound

Product 1

HCID 117642231HCID 117642231, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Peracetic acid (32% in dilute HOAc, 0.12 mL, 0.512 mmol) was added to a solution of (2S,3S,4R,5S,6R)-2-(3-(4-(4-methoxy-4-oxobutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (9, 100 mg, 0.170 mmol) in 1 mL of HOAc and 2 mL of CH3CN at 0° C. The reaction was stirred for 20 min at 0° C. The reaction was quenched with 1N aqueous NaOH, then extracted twice with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and the solvents were removed in vacuo to provide a 2:1 diastereomeric mixture of sulfoxides 60 (60 mg, 58% yield) that was carried to the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d, 2:1 mixture of diastereomers at S, designated as major Ha and minor Hb) δ ppm 7.11-7.17 (m, 2 H), 7.05-7.09 (m, 2 H), 6.97-7.02 (m, 3 H), 5.59 (t, J=9.3 Hz, 1 Hb), 5.46 (t, J=9.3 Hz, 1 Hb), 5.41 (t, J=9.6 Hz, 1 Ha), 5.21 (t, J=9.9 Hz, 1 Ha), 5.17 (t, J=9.3 Hz, 1 Hb), 5.13 (t, J=9.9 Hz, 1 Ha), 4.50 (t, J=10.4 Hz, 1 Ha), 4.48 (d, J=9.9 Hz, 1 Ha), 4.46 (d, J=10.1 Hz, 1 Hb), 4.31 (d, J=10.1 Hz, 1 Hb), 3.93 (m, 2 Hb), 3.92 (m, 2 Ha), 3.66 (s, 3 H), 2.67 (s, 3 Ha), 2.64 (s, 3 Hb), 2.61 (t, J=7.8 Hz, 2 H), 2.33 (t, J=7.3 Hz, 2 H), 2.23 (s, 3 H), 2.09 (s, 3 Ha), 2.08 (s, 3 Hb), 2.02 (s, 3 Hb), 2.01 (s, 3 Ha), 1.93 (quin, J=7.3 Hz, 2 H), 1.75 (s, 3 Ha), 1.74 (s, 3 Hb). MS (ES+) [M+H]+=603.

Workup

  1. customThe reaction was quenched with 1N aqueous NaOH
  2. extractionextracted twice with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customto provide

Sources & evidence

ORD record
ord-afeee499df84421f8e5f67d5b3692b55
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

Loading…