Triethylamine → N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclopropyl]methyl]glycine ethyl ester

HRID 2114844Notes

Reaction equation

HRID 2114844 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH3:8]CN(CC)CC.[CH:15]([C:17]1([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)=O.C([BH3-])#N.[Na+]>CO>[CH2:23]([O:22][C:21]([NH:20][C:17]1([CH2:15][NH:6][CH2:5][C:4]([O:3][CH2:2][CH3:8])=[O:7])[CH2:19][CH2:18]1)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 54500481Benzyl (1-formylcyclopropyl)carbamate

Product 1

HCID 69149507N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclopropyl]methyl]glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of glycine methyl ester hydrochloride (16.24 g, 116.31 mmol) and Et3N (16.21 mL, 116.31 mmol) in MeOH were added a solution of benzyl 1-formylcyclopropylcarbamate (5.10 g, 23.26 mmol) in MeOH (100 mL) and sodium cyanoborohydride (1.83 g, 29.08 mmol). The reaction was stirred at room temperature overnight, and the solvent was removed in vacuo. The resulting residue was suspended in Et2O and washed with aqueous 5% NaOH solution. The aqueous layer was extracted once with Et2O and once with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the product.

Workup

  1. customthe solvent was removed in vacuo
  2. washwashed with aqueous 5% NaOH solution
  3. extractionThe aqueous layer was extracted once with Et2O and once with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the product

Sources & evidence

ORD record
ord-4fa0be30d7404f3187cd4de6796d217e
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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