Dimethyl Sulfide → Ethyl N-(2-{(tert-butoxycarbonyl)[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)glycinate

HRID 1466076Notes

Reaction equation

HRID 1466076 reaction equation
[C:1]([C:3]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH:7]2[CH2:13][N:14]([CH2:22][CH:23]=C)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])#[N:2].O=[O+][O-].CSC.Cl.[NH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C([BH3-])#N.[Na+]>CO.CCOC(C)=O>[C:17]([O:16][C:15]([N:14]([CH2:13][CH:7]1[C:8]2[C:4](=[C:3]([C:1]#[N:2])[C:11]([F:12])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)[CH2:22][CH2:23][NH:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:21])([CH3:18])([CH3:19])[CH3:20]

Participants

8

Reactant 5

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 131732687tert-Butyl [(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]prop-2-en-1-ylcarbamate

Product 1

HCID 89526110Ethyl N-(2-{(tert-butoxycarbonyl)[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)glycinate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-Butyl [(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]prop-2-en-1-ylcarbamate (45 mg, 0.14 mmol) in MeOH (5 mL) was bubbled ozone until the solution turned blue. Excess ozone was removed by bubbling nitrogen through. To the reaction was then added DMS (0.50 ml, 6.8 mmol), and it was allowed to warm to RT. The solvent was removed under reduced pressure, and the resulting material was further treated with ethyl aminoacetate hydrochloride (13 mg, 0.090 mmol) and sodium cyanoborohydride (6.0 mg, 0.090 mmol). When LC showed the reaction was done, the reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and purified by MPLC to deliver the title product. LC-MS (IE, m/z): 420 [M+1]+.

Workup

  1. customExcess ozone was removed
  2. customby bubbling nitrogen through
  3. customThe solvent was removed under reduced pressure
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. custompurified by MPLC

Sources & evidence

ORD record
ord-fd91ffacb4614e99ae75cd48d60fd096
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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