Sodium Carbonate → HCID 178453848, compound

HRID 1053771Notes

Reaction equation

HRID 1053771 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]([C@H:19]1[C:27]2[C:22](=[C:23]([C:28]#[N:29])[CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:31][OH:32].C([O-])([O-])=O.[Na+].[Na+]>CCO>[Si:1]([O:8][CH2:9][CH2:10][N:11]([C@H:19]1[C:27]2[C:22](=[C:23]([C:28](=[NH:29])[NH:31][OH:32])[CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 58344554(R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

Product 1

HCID 178453848HCID 178453848, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Prepared using General Procedure 1. To (R)-tert-butyl 2-(tert-butyldimethyl silyloxy)ethyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate INT-59 (0.800 g, 1.9 mmol) in EtOH (8 mL) was added hydroxylamine hydrochloride (0.400 g, 5.8 mmol) and Na2CO3 (0.610 g, 5.8) and the reaction mixture was heated at 85° C. for 12 h. Once cooled to room temperature, the reaction mixture was filtered using EtOH to rinse the filter cake. The filtrate was concentrated under reduced pressure and washed with EA and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated to produce 0.860 g (100%) of (R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-(N-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl)carbamate INT-61 as a light yellow oil. LCMS-ESI (m/z) calculated for C23H39N3O4Si: 449.7; found 350.2 [M+H−Boc]+, tR=1.97 min.

Workup

  1. customPrepared
  2. temperatureOnce cooled to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washto rinse the filter cake
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washwashed with EA and brine
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1ec3bc8080ad43229f0f0878cd226922
Source dataset
uspto-grants-2016_07
Patent number
US09394264B2

Reaction notes

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