Nitrogen → (S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

HRID 612853Notes

Reaction equation

HRID 612853 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([OH:6])=[O:5].N#N.[CH3:20][C:21](=[CH2:23])[CH3:22].C([O-])(O)=O.[Na+]>O1CCOCC1.C(OCC)C>[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([O:6][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8255Isobutylene2×HCID 516892Sodium BicarbonateHCID 2756313Z-Dap-OH

Product 1

HCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

10 g (42 mmol) of (2S)-3-amino-2-benzyloxycarbonylaminopropionic acid were shaken in an autoclave at 20 atm. N2 pressure for 3 days in a mixture of 100 ml of dioxane, 100 ml of isobutylene and 8 ml of conc. H2SO4Excess isobutylene was blown out and 150 ml of diethyl ether and 150 ml of saturated NaHCO3 solution were added to the remaining solution. The phases were separated and the aqueous phase was extracted twice using 100 ml of diethyl ether each time. The combined organic phases were washed with 2×100 ml of H2O and dried over Na2SO4. After removing the solvent in vacuo, (1.1) were obtained as a pale yellow oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice
  3. washThe combined organic phases were washed with 2×100 ml of H2O
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo

Sources & evidence

ORD record
ord-743896165d4a47869a02afa8e869ab4a
Source dataset
uspto-grants-1999_12
Patent number
US06005117

Reaction notes

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