Potassium Carbonate → HCID 70153605, compound

HRID 2296750Notes

Reaction equation

HRID 2296750 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([C:11](=[O:33])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:32])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:14][CH:13]=2)[C:7]2[CH:34]=[CH:35][CH:36]=[CH:37][C:6]=2[S:5]1.C(OC([NH:45][C:46]([CH3:51])([CH3:50])[C:47](O)=[O:48])=O)(C)(C)C.ON1C2C=CC=CC=2N=N1.[ClH:62].CN(C)CCCN=C=NCC.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[ClH:62].[NH2:45][C:46]([CH3:51])([CH3:50])[C:47]([NH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([C:11](=[O:33])[C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:32])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:16][CH:17]=2)[C:7]2[CH:34]=[CH:35][CH:36]=[CH:37][C:6]=2[S:5]1)=[O:48]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 18387463HCID 18387463, compound

Product 1

HCID 70153605HCID 70153605, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Compound 28 as prepared in Example 14 (0.180 g, 0.36 mM), 2-(tert-butoxycarbonylaminoisobutyric acid (0.072 g, 0.36 mM), 1-hydroxybenzotriazole (0.05 g, 0.36 mM) and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (0.169 g, 0.9 mM) in methylene chloride (30 ml) was stirred at room temperature for 6 hours and a saturated potassium carbonate solution was added. Water was added and the layers were separated. The methylene chloride layer was dried (MgSO4), evaporated in vacuo and the resulting semi-solid purified by chromatography. The BOC group was removed with trifluoroacetic acid to give the desired amine. The HCl salt was prepared and recrystallized from methanol/diethyl ether to give the desired product as a white crystalline solid. m/z (MH+)593.

Workup

  1. customthe layers were separated
  2. dry with materialThe methylene chloride layer was dried (MgSO4)
  3. customevaporated in vacuo
  4. customthe resulting semi-solid purified by chromatography
  5. customThe BOC group was removed with trifluoroacetic acid

Sources & evidence

ORD record
ord-a3da396a965f424a870b89ec4d5c7749
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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