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

HRID 1258364Notes

Reaction equation

HRID 1258364 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].CCN=C=NC[CH2:31][CH2:32][N:33]([CH3:35])[CH3:34].Cl.C1C=[C:41]2[N:43]=NN(O)C2=CC=1.[OH2:47].CCN(C(C)C)C(C)C.C(Cl)Cl.[CH2:60]1[CH2:64][O:63][CH2:62][CH2:61]1>O.C(Cl)Cl>[CH2:62]([O:63][C:35]([N:33]1[CH2:32][CH2:31][N:43]([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])[CH2:41][CH2:34]1)=[O:47])[CH2:61][CH2:60][CH3:64]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1074725-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21919333Tetrahydrofurane dichloromethane

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Z-(L)Glu(OtBu)-OH (25.2 g) in DCM/THF (240 mL/60 mL) were added EDCI hydrochloride (17.2 g), HOBT hydrate (13.7 g) and DIPEA (28.2 mL). After stirring at RT for 5 min, intermediate 1.2 (20 g) was added. The mixture was stirred at RT overnight. DCM and water were added and the phases were separated. The org. phase was washed with 2M Na2CO3, with 1M NaHSO4 and with brine, was dried (Na2SO4) and evaporated off. Drying under HV gave the desired compound as an orange oil (40 g).

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. customthe phases were separated
  3. washphase was washed with 2M Na2CO3, with 1M NaHSO4 and with brine
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated off
  6. customDrying under HV

Sources & evidence

ORD record
ord-22cb68b5657c49529f87ffd97214730e
Source dataset
uspto-grants-2013_06
Patent number
US08466156B2

Reaction notes

Loading…