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

HRID 1935334Notes

Reaction equation

HRID 1935334 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 (2S)-3-amino-2-benzyloxycarbonylaminopropionic acid were shaken for 3 days, in an autoclave and under 20 atm. N2 pressure, in a mixture of 100 ml of dioxane, 100 ml of isobutylene and 8 ml of conc. H2SO4. Excess isobutylene was blown off, and 150 ml of diethyl ether and 150 ml of a saturated solution of NaHCO3 were added to the remaining solution. The phases were separated and the aqueous phase was extracted 2 times with 100 ml of diethyl ether on each occasion. The combined organic phases were washed with 2×100 ml of H2O and dried over Na2SO4. After the solvent had been removed in vacuo, 9.58 g (78%) of (1.6) were obtained as a pale yellow oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted 2 times with 100 ml of diethyl ether on each occasion
  3. washThe combined organic phases were washed with 2×100 ml of H2O
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent had been removed in vacuo

Sources & evidence

ORD record
ord-357e392b2aa5466987776e21a074161a
Source dataset
uspto-grants-2002_05
Patent number
US06387895B1

Reaction notes

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