Diisopropylethylamine → HCID 69904020, compound

HRID 841142

Reaction equation

HRID 841142 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[NH:17]([C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[C@H:18]([C:44](O)=[O:45])[CH2:19][C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C)C=O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]([C:44](=[O:45])[C@@H:18]([NH:17][C:47]([O:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:48])[CH2:19][C:20]1[N:24]=[CH:23][N:22]([C:25]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:21]=1)[CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10889780Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinateHCID 15545280Z-His(Trt)-OH

Product 1

HCID 69904020HCID 69904020, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Step 1 (0.67 g, 2.5 mmol) was dissolved in methylene chloride (10 mL) and Cbz-His(Trt)-OH (1.46 g, 2.75 mmol) was then added, followed by diisopropylethylamine (1.3 mL, 7.5 mmol), HATU (1.05 g, 2.76 mmol), HOAt (0.374 g, 2.75 mmol), and dimethylformamide (10 mL). The reaction was stirred overnight at room temperature. The solution was concentrated, the residue taken up in ethyl acetate and washed three times with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo to give a white solid; 1.8 g (97% yield). MS-APCI: M+1=747.

Workup

  1. concentrationThe solution was concentrated
  2. washwashed three times with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid

Sources & evidence

ORD record
ord-9fc0a3a4702141aead5356724a700604
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Linked notes

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