Diisopropylethylamine → 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

HRID 2063448Notes

Reaction equation

HRID 2063448 reaction equation
[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH:25]1[CH:30]=C2N=NN(O)C2=[CH:27][CH:26]=1.O.CCN=C=NC[CH2:42][CH2:43][N:44]([CH3:46])C.Cl.C[CH2:49][N:50](C(C)C)C(C)C.[C:57]([O-:60])(O)=[O:58].[Na+]>C(Cl)Cl.C1COCC1.C(Cl)Cl>[CH2:30]([O:60][C:57]([N:44]1[CH2:43][CH2:42][N:50]([C:12](=[O:14])[C@@H:2]([NH:1][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3][CH2:4][C:5]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:11])[CH2:49][CH2:46]1)=[O:58])[CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1074725-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamateHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 451403594-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Cbz-(L)Glu(OtBu)-OH (10 g), HOBT hydrate (5 g), EDCI hydrochloride (6.3 g), intermediate 1.4 (6 g) and DIPEA (10 mL) were dissolved in DCM/THF (1/1, 84 mL). The mixture was stirred at RT for 1 h. DCM and an aq. NaHCO3 solution were added to the mixture and the phases were separated. The org. phase was washed with a 1M NaHSO4 solution, dried (Na2SO4) and evaporated off. CC of the crude (EA/Hept 1/2) offered 13.8 g of the desired compound.

Workup

  1. customthe phases were separated
  2. washphase was washed with a 1M NaHSO4 solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated off

Sources & evidence

ORD record
ord-51d88012dbf54d53990a2407af394703
Source dataset
uspto-grants-2012_10
Patent number
US08288385B2

Reaction notes

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