Formaldehyde → HCID 18973009, compound

HRID 2394306Notes

Reaction equation

HRID 2394306 reaction equation
[C:1]([BH3-])#N.[Na+].C=O.[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:20][N:21]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)[CH3:1])[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18972948HCID 18972948, compound

Product 1

HCID 18973009HCID 18973009, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium cyanoborohydride (121 mg) was added to a solution of formaldehyde (570 mg), methyl 2-(tert-butoxycarbonylamino)-3-(3,4-dichlorobenzylamino)propionate (720 mg) and acetic acid (0.1 ml) in acetonitrile and the mixture was stirred at room temperature for 30 minutes. Aqueous sodium hydrogen carbonate (10 ml) was added and the mixture was extracted with ethyl acetate (3×20 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colourless oil (722 mg). NMR δH (360 MHz, CDCl3) 1.45 (9H, s), 2.21 (3H, s), 2.73 (2H, d, J=7.0 Hz), 3.46 (2H, m), 3.75 (3H, s) 4.37 (1H, m), 5.19 (1H, br s), 7.10 (1H, dd, J=11.0 and 1.0 Hz), 7.36 (2H, m).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-00cbde4d8b4d4695be3e43becebbcf10
Source dataset
uspto-grants-1998_09
Patent number
US05811431

Reaction notes

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