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

HRID 324591Notes

Reaction equation

HRID 324591 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+]>C(OCC)C.O1CCOCC1>[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 (2S)-3-amino-2-benzyloxycarbonylaminopropionic acid are shaken in an autoclave for 3 days, at an N2 pressure of 20 atm., in a mixture consisting of 100 ml of dioxane, 100 ml of isobutylene and 8 ml of conc. H2SO4. Excess isobutylene is blown off and 150 ml of diethyl ether and 150 ml of a saturated solution of NaHCO3 are added to the remaining solution. The phases are separated and the aqueous phase is extracted twice with 100 ml of diethyl ether on each occasion. The combined organic phases are washed with 2×100 ml of H2O and dried over Na2SO4. 9.58 g (78%) of (1.6) are obtained as a pale yellow oil after the solvent has been removed in vacuo.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted twice with 100 ml of diethyl ether on each occasion
  3. washThe combined organic phases are washed with 2×100 ml of H2O
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fd26fc5431d5450c8efeda5ac752b387
Source dataset
uspto-grants-2001_04
Patent number
US06218415B1

Reaction notes

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