Sodium Thiosulfate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(heptane-1-sulfonyl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

HRID 1779178Notes

Reaction equation

HRID 1779178 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]SCCCCCCC)[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[CH:51]1[CH:56]=[C:55](Cl)[CH:54]=[C:53]([C:58](OO)=O)[CH:52]=1.[S:62]([O-:66])([O-])(=[O:64])=S.[Na+].[Na+]>ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][S:62]([CH2:58][CH2:53][CH2:52][CH2:51][CH2:56][CH2:55][CH3:54])(=[O:66])=[O:64])[C@@:22]([OH:34])([CH2:30][CH2:31][O:32][CH3:33])[C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 118260126tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-heptylsulfanyl-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

Product 1

HCID 118260127tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(heptane-1-sulfonyl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-heptylsulfanyl-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (No. 6804240; 50.9 mg, 0.0709 mmol) was dissolved in dichloromethane (3.4 mL), and the mixture was cooled to 0° C. mCPBA (72% content, 34.0 mg, 0.142 mmol) was added, and the mixture was stirred at 0° C. for 30 minutes. After completing the reaction, the progress of the reaction was stopped by adding an aqueous solution of 10% sodium thiosulfate, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water, and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 56.1 mg of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(heptane-1-sulfonyl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (No. 6804464; ESI (LC/MS positive mode) m/z 750 (M+H); Rt 2.15 min.).

Workup

  1. additionwas added
  2. customthe reaction
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water
  5. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e206c90846b4dd4a5a133b505643b14
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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