Sodium Cyanide → HCID 68349493, compound

HRID 72340Notes

Reaction equation

HRID 72340 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:10][CH2:11]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:23]#[N:24].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:10][CH2:11][C:23]#[N:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86652874methanesulfonic acid (S)-3-tert-butoxycarbonylamino-3-phenylpropyl ester

Product 1

HCID 68349493HCID 68349493, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methanesulfonic acid (S)-3-tert-butoxycarbonylamino-3-phenylpropyl ester (2.0 g) and sodium cyanide (0.97 g) in DMF (10 ml) was stirred at 70° C. for 16 hours. The reaction mixture was partitioned between water (50 ml) and ethyl acetate (50 ml), and the aqueous phase was reextracted (2×50 ml). The combined organic phases were dried over magnesium sulfate and concentrated. This gave the product (1.7 g) with a molecular weight of 260.3 g/mol (C15H20N2O2); MS (ESI): m/e=261 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between water (50 ml) and ethyl acetate (50 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e67ae3b38284fe8aaf463011bee7990
Source dataset
uspto-grants-2014_09
Patent number
US08828995B2

Reaction notes

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