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

HRID 1057300Notes

Reaction equation

HRID 1057300 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].OS(O)(=O)=O.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

8

Reactant 5

HCID 947NitrogenHCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 516892Sodium BicarbonateHCID 2756313Z-Dap-OH

Product 1

HCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoateYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

10 g (42 mmol) of (S)-3-Amino-2-benzyloxycarbonylaminopropionic acid were shaken in an autoclave at an N2 pressure of 20 atm for 3 days in a mixture of 100 ml of dioxane, 100 ml of isobutylene and 8 ml of conc. H2SO4 . Excess 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 2× with 100 ml of diethyl ether each time. The combined organic phases were washed with 2×100 ml of water and dried over Na2SO4. After removing the solvent in vacuo, 9.58 g (78%) of the title compound were obtained as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-f4a0d51590cd400bb3ac45f0753b7a53
Source dataset
uspto-grants-2003_02
Patent number
US06514952B1

Reaction notes

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