Dimethyl Sulfide → HCID 87354684, compound

HRID 61420Notes

Reaction equation

HRID 61420 reaction equation
[CH2:1]([C@@H:4]([C@H:12]([CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:13]([O:15][CH3:16])=[O:14])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH:2]=C.[O:36]=[O+][O-].CSC>ClCCl>[CH2:29]([N:18]([CH2:17][C@@H:12]([C@H:4]([CH2:1][CH:2]=[O:36])[C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:13]([O:15][CH3:16])=[O:14])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 67321975HCID 67321975, compound

Product 1

HCID 87354684HCID 87354684, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-methyl 1-tert-butyl(2S,3R)-2-allyl-3-({benzyl[(benzyloxy)cabonyl]amino}methyl)butanedioate (2.336 g, 4.851 mmol) in dichloromethane (97 mL) at −78° C. was bubbled ozone. After the solution turned blue, ozone bubbling continued for additional 15 min. Nitrogen was then bubbled into the mixture until the blue color disappeared. The reaction was quenched with dimethyl sulfide (1.78 mL, 24.26 mmol) and the solution was stirred at rt for 2 h. The solvent was removed under reduced pressure and the residue was purified by Combiflash (15-25% EtOAc/hexane) to provide 1.853 g (79%) of 1-methyl 4-tert-butyl(2R,3S)-2-({benzyl[(benzyloxy)cabonyl]amino}methyl)-3-(2-oxoethyl)butanedioate as a colorless viscous oil (1.853 g, 79% in yield). MS (ESI): 506.1 (M+Na+).

Workup

  1. customNitrogen was then bubbled into the mixture until the blue color
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by Combiflash (15-25% EtOAc/hexane)
  4. customto provide

Sources & evidence

ORD record
ord-433f0b7f3c5e4d0d8ca0bff9f1f78d95
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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