Azide → HCID 131720714, compound

HRID 963952Notes

Reaction equation

HRID 963952 reaction equation
[NH2:1][C@H:2]([C:9]([NH:11][C@H:12]([C:20]([NH2:22])=[O:21])[CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.Cl.[NH:25]([C:39]([CH3:41])=[O:40])[C@H:26]([C:36](O)=[O:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C.[N-]=[N+]=[N-]>CN(C)C=O>[NH:25]([C:39]([CH3:41])=[O:40])[C@H:26]([C:36]([NH:1][C@H:2]([C:9]([NH:11][C@H:12]([C:20]([NH2:22])=[O:21])[CH2:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 33558AzideHCID 81531DiisopropylethylamineHCID 11085640(S)-2-Acetamido-3-(4-cyanophenyl)propanoic acidHCID 131720713HCID 131720713, compound

Product 1

HCID 131720714HCID 131720714, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir overnight H-(L)-Chg-(L)-Pal-NH2.2HCl (1.13 g, 3 mmol), Ac-(L)Phe(4-CN)-OH (0.84 g, 3.6 mmol), diisopropylethylamine (10 mmol). and diphenylphoshoryl azide (803 μl 3.6 mmol) dimethyl formamide (30 mL) overnight. Evaporate dimethyl formamide, precipitate by ether, filter and wash by ether to give Ac-(L)-Phe(4-CN)-(L)-Chg-(L)-Pal-NH2 (1.282 g, 82%). ##STR21##

Workup

  1. filtrationEvaporate dimethyl formamide, precipitate by ether, filter
  2. washwash by ether

Sources & evidence

ORD record
ord-a0bf2bac88774984b038ae288f88a234
Source dataset
uspto-grants-1998_06
Patent number
US05766932

Reaction notes

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