Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68000904, compound

HRID 931915Notes

Reaction equation

HRID 931915 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[C@@H:7]([N:10]1[C@H:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C@@H:14]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH2:13][C@H:12]([CH2:30][CH:31]=[CH2:32])[C:11]1=[O:33])[CH2:8][CH3:9])(=[O:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClC(Cl)C.O>[CH2:30]([C@H:12]1[CH2:13][C@H:14]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C@@H:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:10]([C@H:7]([C:6]2[O:3][C:1]([CH3:2])=[N:4][N:5]=2)[CH2:8][CH3:9])[C:11]1=[O:33])[CH:31]=[CH2:32]

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68000416HCID 68000416, compound

Product 1

HCID 68000904HCID 68000904, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 58 mg (0.115 mmol) of (S)-N′-acetyl-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanehydrazide (Example 34, Step A) and Burgess' reagent (110 mg, 0.462 mmol) in dichloroethane (1154 μL) was heated in the microwave at 120° C. for 30 min. Then the reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with sat. aq. NaCl and NaHCO3-solutions, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Separation by reversed phase HPLC (55 to 90% MeCN/H2O in 35 min, 29 mg injection each time) provided the title compound as a colorless film. MS (ESI) 484.1 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with sat. aq. NaCl and NaHCO3-solutions
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customSeparation by reversed phase HPLC (55 to 90% MeCN/H2O in 35 min

Sources & evidence

ORD record
ord-2bf45969b4db4cb2bc24728c67b98194
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

Loading…