Hydrochloric Acid → HCID 59323649, compound

HRID 1911543Notes

Reaction equation

HRID 1911543 reaction equation
C(O[C:6](=[O:21])[NH:7][C@H:8]([CH2:19]O)[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])=[O:11])(C)(C)C.Cl.C([O-])([O-])=O.[K+].[K+].[N:29]#CBr>C(O)C>[C:13]1([S:10]([CH2:9][C@H:8]2[CH2:19][O:21][C:6]([NH2:29])=[N:7]2)(=[O:11])=[O:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 11120630HCID 11120630, compound

Product 1

HCID 59323649HCID 59323649, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

((R)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester (0.29 g, 0.92 mmol) was dissolved in ethanol (2 ml), hydrochloric acid in ethanol (5M, 5 ml) was added and the mixture was stirred at 60° C. for 3 hours. The solvent was evaporated and the residue was taken up in tetrahydrofuran (5 ml). K2CO3 (0.326 g, 2.36 mmol) and cyanogen bromide (0.136 g, 1.29 mmol) were added. The mixture was stirred overnight and afterwards partitioned between ethyl acetate and water. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (SiO2, EtOAc/MeOH=95:5 to yield a white solid, (0.062 g, 28%); MS (ISP): 241.1 ((M+H)+.).

Workup

  1. customThe solvent was evaporated
  2. stirringThe mixture was stirred overnight
  3. customafterwards partitioned between ethyl acetate and water
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (SiO2, EtOAc/MeOH=95:5
  8. customto yield a white solid, (0.062 g, 28%)

Sources & evidence

ORD record
ord-2c3f2ae4e40747cf8f3cf257a18436d7
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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