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

HRID 439307

反応式

HRID 439307 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e434807956948878cfe5375017dd202
出典データセット
uspto-grants-1996_05
特許番号
US05514654

関連ノート

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