Sodium cyanoborohydride → ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionate

HRID 271851Notes

Reaction equation

HRID 271851 reaction equation
Cl.CN.[C:4]([O:8][C:9]([NH:11][C@@H:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]=O)[CH:26]=2)=[CH:21][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])([CH3:7])([CH3:6])[CH3:5].[C:33]([BH3-])#[N:34].[Na+]>CO>[C:4]([O:8][C:9]([NH:11][C@@H:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][NH:34][CH3:33])[CH:26]=2)=[CH:21][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 86601619ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-formylbiphenyl-4-yl)propionate

Product 1

HCID 69685901ethyl (S)-2-tert-butoxycarbonylamino-3-(3'-methylaminomethylbiphenyl-4-yl)propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.2 g (314 mmol) of methylamine hydrochloride are introduced into a solution containing 25 g (63.0 mmol) of ethyl (S)-2-tert-butoxycarbonylamino-3-(3′-formylbiphenyl-4-yl)propionate in 200 ml of methanol. After stirring for 30 min at ambient temperature, 6.0 g (95.4 mmol) of sodium cyanoborohydride are added portionwise. The reaction medium is stirred for 16 h and the solvents are evaporated off. The residue is dissolved in ethyl acetate, and the organic phase is washed with water and then dried over magnesium sulfate and concentrated.

Workup

  1. stirringThe reaction medium is stirred for 16 h
  2. customthe solvents are evaporated off
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-acf9e2ab77c64fbf880a9dca50467828
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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