Sodium Thiosulfate → HCID 86694363, compound

HRID 538932Notes

Reaction equation

HRID 538932 reaction equation
[OH:1][CH2:2][C@@H:3]([N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].C([O-])(O)=O.[Na+].[O-]Cl.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:5]([C@@H:3]([CH3:4])[CH:2]=[O:1])[C:6](=[O:15])[O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 86694364HCID 86694364, compound

Product 1

HCID 86694363HCID 86694363, compoundYield 96.4%

Reagents, catalysts & solvents 3

HCID 253877Potassium BromideCatalystHCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (S)-benzyl (1-hydroxypropan-2-yl)(4-methoxybenzyl)carbamate (11.8 g, 35.5 mmol) in CH2Cl2 was added NaHCO3 (3.28 g, 39 mmol), KBr (0.25 g, 2.1 mmol) and TEMPO 0.168 g, 1.07 mmol). The reaction mixture was cooled to 0-5° C. and the 5% aqueous NaClO solution (85 mL, 71 mmol) was added within 30 min. After stirring for 1 h at 0-5° C. the reaction mixture was added to Na2S2O3 solution and the product was extracted with EtOAc. Combined extracts were washed with aqueous NaH2PO4 solution, H2O and brine, dried over MgSO4, filtered and concentrated to provide the title compound as a yellow oil (11.2 g, 96%): TLC (hexane/EtOAc 1:1) Rf=0.55; tR=1.29 min (UPLC 1), tR, 1.15 min (LC-MS 3); ESI-MS: 328 [M+H]+ (LC-MS 3).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washCombined extracts were washed with aqueous NaH2PO4 solution, H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f28a4671161e4b238430e98b1a8addef
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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