Ethyl isocyanatoacetate → Methyl (2S)-ethyloxycarbonylmethylaminocarbonylamino-3-tert-butoxycarbonylaminopropionate

HRID 324592Notes

Reaction equation

HRID 324592 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:2]=[O:3].Cl.[NH2:11][C@@H:12]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]([O:15][CH3:16])=[O:14]>O1CCCC1>[CH2:8]([O:7][C:5]([CH2:4][NH:1][C:2]([NH:11][C@@H:12]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]([O:15][CH3:16])=[O:14])=[O:3])=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

Product 1

HCID 86583696Methyl (2S)-ethyloxycarbonylmethylaminocarbonylamino-3-tert-butoxycarbonylaminopropionateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.13 ml (45.8 mmol) of ethyl isocyanatoacetate are added dropwise to a suspension of 10 g (45.8 mmol) of the compound (3.3) in 100 ml of tetrahydrofuran and the mixture is left to stir at room temperature for 3 h; the solvent is removed in vacuo and the residue is chromatographed through silica gel using ethyl acetate/methanol =20/1. 13.44 g (85%) of (3.4) are obtained as a pale yellow oil.

Workup

  1. waitthe mixture is left
  2. customthe solvent is removed in vacuo
  3. customthe residue is chromatographed through silica gel

Sources & evidence

ORD record
ord-831b016db4fe44d39baa707c42c20f35
Source dataset
uspto-grants-2001_04
Patent number
US06218415B1

Reaction notes

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