Triethylamine → N-(7-oxododecanoyl)-L-alanyl-D-isoglutamine benzyl ester

HRID 439307

Reaction equation

HRID 439307 reaction equation
[O:1]=[C:2]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:13]([OH:15])=O)[CH3:12])=[O:9].Cl.[CH2:22]([O:29][C:30](=[O:38])[CH2:31][CH2:32][C@H:33]([C:35](=[O:37])[NH2:36])[NH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C1C=CC=CC=1>[CH2:22]([O:29][C:30](=[O:38])[CH2:31][CH2:32][C@H:33]([C:35](=[O:37])[NH2:36])[NH:34][C:13](=[O:15])[C@H:11]([CH3:12])[NH:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22802678D-Isoglutamine benzyl ester hydrochlorideHCID 54199880N-(7-oxododecanoyl)-L-alanine

Product 1

HCID 22860847N-(7-oxododecanoyl)-L-alanyl-D-isoglutamine benzyl ester

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-(7-oxododecanoyl)-L-alanine (590 mg, 2.07 mmoles) and D-isoglutamine benzyl ester hydrochloride (565 mg, 2.07 mmoles) were dissolved in N,N-dimethylformamide (7 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (578 mg, 2.1 mmoles) and triethylamine (424 mg, 4.2 mmoles) were added thereto. The reaction mixture was stirred for 1 hour on an ice bath and for another 48 hours at room temperature. To the resulting suspension there were added benzene (5 ml) and ethyl acetate (25 ml) and it was washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the compound was precipitated from n-hexane/diethyl ether.

Workup

  1. washwas washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customthe compound was precipitated from n-hexane/diethyl ether

Sources & evidence

ORD record
ord-3e434807956948878cfe5375017dd202
Source dataset
uspto-grants-1996_05
Patent number
US05514654

Linked notes

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