Sodium Cyanide → HCID 66674018, compound

HRID 421935Notes

Reaction equation

HRID 421935 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:38]([O:40][CH3:41])=[O:39])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:42]#[N:43].[Na+]>CN(C=O)C>[C:42]([CH2:26][CH:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:38]([O:40][CH3:41])=[O:39])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)#[N:43]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 87101148HCID 87101148, compound

Product 1

HCID 66674018HCID 66674018, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 14-cyclohexyl-7(R,S)-({[(4-methylphenyl)sulfonyl]oxy}methyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.35 M) in DMF was treated with NaCN (1.2 eq.) and the resulting mixture was stirred overnight at RT. The reaction was quenched by addition of sat. aq. NaHCO3 and extracted into EtOAc. The combined organic layers were washed with brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by FC (PE/EtOAc 90:10) affording the product as a yellow foam (90%). (ES+) m/z 429 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of sat. aq. NaHCO3
  2. extractionextracted into EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by FC (PE/EtOAc 90:10)

Sources & evidence

ORD record
ord-9b17f77a0b38493ca9353b605e308884
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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